Methyl 2-phenoxyacetate

clear colorless liquid

9.4 g of phenol 1-1 was dissolved in 100 MlN, N-dimethylformamide, 11.9 g of methyl chloroacetate and 20.7 g of potassium carbonate were added, respectively. The reaction system was heated to 50 ° C and stirred for 12 h. The reaction was followed by TLC. After the reaction was over, the reaction system was added.300 mL of ice water. The aqueous phase was extracted twice with 200 mL of ethyl acetate.The organic phase was washed three times with 400 mL of brine and dried over anhydrous sodium sulfate.After drying the solvent under reduced pressure, the residue was purified by silica gel column chromatography ( petroleum ether:Ethyl acetate = 20: 1) to give 15.2g as a light yellow oil 2. The yield was 92.0percent.To a stirred solution of phenol (4) (1.0 g, 10.67 mmol) in DMF was added KTo 95.06 g of 99percent phenol was added 42.83 g of 99percent sodium hydroxide and 142.59 gXylene, heated and refluxed to reduce water to ≤0.5percent, 116.20 g of 99percent methyl chloroacetate was added dropwise thereto at 90 ° C to cause a reaction.After the addition is completed, the temperature is kept at this temperature for 0.5 h.The mixture is cooled to 40 ° C and filtered, and an appropriate amount of xylene is used to wash the filter cake, and then dried to obtain sodium chloride and methyl phenoxyacetate containing xylene.Distillation of xylene to obtain 172.02 g of methyl phenoxyacetate.The content is 96.1percent.To 950.6 g of 99percent pure phenol, 428.3 g of 99percent pure sodium hydroxide and 1425.9 g of xylene were added, and the mixture was heated and refluxed to a water content of ≤0.5percent.1162.0 g of 99percent pure methyl chloroacetate was added dropwise at 90 ° C to react, and the reaction was kept at this temperature for 0.5 h.The temperature is lowered to 40 ° C, filtered, and the filter cake is washed with an appropriate amount of xylene, and then dried to obtain a crude product of sodium chloride and methyl phenoxyacetate containing xylene.The xylene was recovered by distillation, and 1720.2 g of methyl phenoxyacetate was obtained at a content of 96.1percent.To 95.06 g of 99percent phenol was added 42.83 g of 99percent sodium hydroxide and 142.59 g of xylene.Heating and refluxing to reduce water to ≤0.5percent, 116.20 g of 99percent methyl chloroacetate was added dropwise thereto at 90 ° C to cause a reaction.After the addition is completed, the temperature is kept at this temperature for 0.5 h.The mixture is cooled to 40 ° C and filtered, and an appropriate amount of xylene is used to wash the filter cake, and then dried to obtain sodium chloride and methyl phenoxyacetate containing xylene.Distillation of xylene to obtain 172.02 g of methyl phenoxyacetate.The purity is 96.1percent.General procedure: (1) An ozone–oxygen mixture was bubbled through a solution of 10.00 mmol of ethers Ia or Ib in a mixture of 20 mL of 2.5 M NaOH in MeOH and 80 mL of CHGeneral procedure: To a mixture oftrimethylphosphite/triethylphosphite (1.0mmol) and carboxylic acid (1.0mmol), 1, 3-diazidopropane (0.5mmol) was added slowly in a drop wise manner (to avoidaccumulation of azide) and the mixture was stirred at room temperature for10-20 minutes. (Caution As azides arepotentially explosive, all the reactions should be carried out behind a blastshield with personal protective equipment. In particular, the sequence of addition of thereactants should be strictly followed to avoid the accumulation of organicazides. This has been achieved in thepresent investigation by the slow drop wise addition of the bis azide to thereaction mixture containing trialkylphosphite during which the azide group isinstantaneously converted to iminophosphorane and hence no difficulty wasencountered). After the completion ofthe reaction (as monitored by TLC), the mixture was poured onto crushedice. Then the reaction mixture wasextracted with dichloromethane and the organic layer was dried over anhydrousNaGeneral procedure: (2) An ozone–oxygen mixture was bubbled through a solution of 10.00 mmol of ethers Ia or Ib in50 mL of MeOH at –78°C until blue color appeared.The reaction mixture was purged with argon, 3.88 g(35.00 mmol) of NH2C(O)NHNH2 HCl. HCl was added at –50°C. The mixture was stirred at ambient temperature for 24 h. The reaction mixture was evaporated, the residue was dissolved in 100 mL of CHCl3, washed with 2 (to pH ≈ 7), and dried with Na2SO4. After evaporation, ether I produced 1.86 g of a mixture of compounds II and IV in 40 : 60 ratio(according to GLC and NMR), column chromatography (Si2, PE, PE : MTBE = 5 : 1, 4 : 1) afforded0.74 g (42percent) of ester IIa and 1.09 g (56percent) of acetal IV.After evaporation, ether Ib produced 1.64 g of a mixture of compounds IIb and IVb in 25 : 75 ratio (according to GLC and NMR data), column chromatography (Si2, PE, PE : MTBE = 5 : 1, 4 : 1) gave 0.40 g (24percent)of ester IIb and 1.15 g (63percent) of acetal IVb.General procedure: A mixture of the amide (1, 1 mmol), alcohol (15 mL), and pulverized potassium bisulfate (1.1 g, 8 mmol) was refluxed for the specified time. The alcohol was removed in vacuo and the residue was triturated with hexanes (or other appropriate solvent such as DCM or ethyl acetate to dissolve the product). Removal of hexanes in vacuo provided the following pure products

Molecular Weight:166.17
XLogP3:1.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:166.062994177
Monoisotopic Mass:166.062994177
Topological Polar Surface Area:35.5
Heavy Atom Count:12
Complexity:139
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes