Propyl 4-methylbenzenesulfonate

clear light yellow liquid

A thermometer in 100 mL 3-neck flask and stirred insert the dichloromethane 20 mL and using an ice-bath the inner temperature of 0 to 5°C. Here para-toluenesulfonic acid monohydrate 380.44 mg (2.0 mmole) and bis (trichloromethyl) carbonate, 236mg (0.80 mmole, 0.40 molbae) and tribasic potassium monohydrate (K[00263] - Industrial scale preparation of propyl tosylate:; A 100 L glass, jacketed reactor was charged with 1-propanol (2.098 kg; 34.9 mol), triethylamine (4.585 kg; 45.3 mol; 1.3 equivalents) and DCM (20.1 L). The mixture was cooled to a temperature of about 5C to 15C and cautiously charged with a solution of /Moluenesulfonyl chloride (6 kg; 31.47 mol; 0.9 equivalents) in DCM (10.5 L) over 30 minutes. Once the addition was complete, the mixture was warmed to a temperature of about 18C to 22C and stirred for 12 hours. The reaction mixture was assayed by EXAMPLE 20Industrial scale preparation of propyl tosylate[00184] A 100 L glass, jacketed reactor was charged with 1-propanol (2.098 kg;34.9 mol), triethylamine (4.585 kg; 45.3 mol; 1.3 equivalents) and DCM (20.1 L). The mixture was cooled to a temperature of about 5° C to 15° C and cautiously charged with a solution of p-toluenesulfonyl chloride (6 kg; 31.47 mol; 0.9 equivalents) in DCM (10.5 L) over 30 minutes. Once the addition was complete, the mixture was warmed to a temperature of about 18° C to 22° C and stirred for 12 hours. The reaction mixture was assayed by NMR (in CDCI3) and deemed complete. HC1 (6 N; 2.98 L) was cautiously charged while maintaining the temperature below 25° C. The aqueous phase was removed, and the organic phase was washed 2 X with water (21 L each wash), dried with MgSC4, and filtered over Celite.(R).. The filtered solids were then washed with DCM (4 L) and concentrated to a residue. The residue was dissolved in heptane and concentrated again to afford a final propyl tosylate product (6.385 kg, 95percent yield).Tetrakis(2-pyridyl)porphyrin, H2T-2-PyP was purchased from Mid-Century Chemicals, [CHICAGO, ] IL. The increased lipophilicity of the [N-PROPYL, ] n-butyl, n-hexyl, and n-octyl analogues required a slight modification of the synthetic approach used for methyl and [ETHYL COMPOUNDS. 4, 12] Typically, 100 mg of [H2T-2-PYP] was dissolved in 20 mL of [DMF] at [100 °C, ] followed by the addition of 4 mL of the corresponding [P-TOLUENESULFONATE.] The course of N-alkylation was followed by thin-layer chromatography on silica gel TLC plates using 1 : 1: 8 [UTO3-SARURATED] [H20] : H2O : acetonitrile as a mobile phase. While complete N-alkylation is achieved within a few hours for the methyl analogue, the required time gradually increases and it took three and five days to prepare the n-hexyl and n-octyl compounds, respectively. Upon completion, for the methyl, ethyl and n-propyl compounds, the reaction mixture was poured into a separatory funnel containing 200 [ML] each of water and chloroform and shaken well. The chloroform layer was discarded and the extraction with [CHC13] was repeated several times. The n-butyl, n-hexyl and n-octyl analogues are more lipophilic and tended to remain in the chloroform layer. Therefore, increasing amounts of methanol were added to the water/CHCl3 mixture in order to force the porphyrin into the [AQUEOUS/METHANOL] layer. This layer was filtered and the porphyrin was precipitated as the [PUS SAUT] by the addition of a concentrated aqueous solution [OF NSPF6.] The precipitate was thoroughly washed with 1 : [1] 2-propanol : diethylether in the case of methyl and ethyl compounds and with pure diethylether for the others. The precipitate was then dissolved in acetone, filtered and precipitated as the chloride salt by the addition of tetrabutylammonium chloride dissolved in. acetone. The precipitate was washed thoroughly with acetone, and dried in vacuo at room temperature. Elemental analysis: H2TnPr-2-PyPCl4 x [12.] [5] [H-20] (C52H71N8O12.5Cl4) : Found: C, 54. 2 ; H, 6.42 ; N, 9. 91 ; Cl, 12. 04. Calculated : C, 54. [20] ; H, 6. 18 ; N, 9.68 ; [CI, ] [12.] 25. [H2TNBUT-2-PYPCL4 X 10.] 5 H20 [(CSNSOCU) : FOUND] : C, 57.16 ; H, 6.94 ; N, 9.513 ; Cl, 1.77. Calculated : C, 57.10 ; H, 6. 41 ; N, 9. 51 ; Cl, [12.] 03. H2TnHex-2-PyPCl4 x 11 H2O (C64H100N8O11Cl4) : Found: C, [59.] 19 ; H, 7. 31 ; N, 8. 61 ; Cl, 11.09. Calculated: C, 59.16 ; [H, ] 7. 751 ; [N, ] 8.60 ; CI, 10.91. [HZTNOCT-2-PYPCID] x 13.5 [HAC] (C64H121N8O13.5Cl4) : Found : C, 59.37 ; H, 7.41 ; [N, ] 7.73. Calculated: C, 59.37 ; H, 8. 37 ; N, 7.69.

Molecular Weight:214.28
XLogP3:2.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:214.06636548
Monoisotopic Mass:214.06636548
Topological Polar Surface Area:51.8
Heavy Atom Count:14
Complexity:245
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes