1-(3-Hydroxy-4-methoxyphenyl)ethanone

3-Hydroxy-4-methoxyacetophenone(Acetoisovanillone; Isoacetovanillone) is an active compound isolated from P. spinosa. Isoacetovanillone possesses anti-inflammatory activity and prevented injuries due to administration of acetic acid in the colon[1].

Isoacetovanillone is a member of phenols and a member of methoxybenzenes. It has a role as a metabolite.

3'-Hydroxy-4'-methoxyacetophenone (12); A solution of ketone 8 (250 mg, 1.20 mmol) in dry CHA solution of ketone 6b (12.5 g, 69.5 mmol) in concentrated H2SO4 (62.5 mL) wasstirred at 65 °C for 46 h. After cooling the reaction mixture to ambient temperature, it was poured onto ice (250 g) and stirred for 1 h.The precipitate was filtered off, washed with water and redissolved in 1M aqueous NaOH (16 mL, 160 mmol). The mixture wasextracted with DCM (65 mL). The aqueous layer was acidified with concentrated HCl (25 mL), stirred for 1.5 h and the precipitatewas filtered off to give 5.39 g (47percent) of the phenol as brown solid with mp 80–81 °C (lit. [11] reports 88–90 °C). 1H NMR data are inaccordance with those published in ref.[11].Dimethoxyacetophenone derivative (I) (72.08 g; 0.4 mol) was dissolved in sulfuric acid (360 ml), and then the mixture was stirred at 62 - 64 °C for 48 h. The reaction mixture was cooled to room temperature, poured into ice water (prepared from 2 kg of ice and 1.6 kg of water) and kept in a refrigerator overnight. The product was collected by filtration, washed with water (5x100 ml) and dried in vacuum at 40 °C until constant weight to obtain the product (40.4 g; 60.2 percent; HPLC purity: 96.4 percent). The crude product was dissolved in warm ethanol (80 ml) and precipitated by addition of n-heptane (80 ml). The mixture was cooled to 0 - 10 °C, stirred at this temperature for 1 h, the product was collected, washed with n-heptane (40 ml) and dried in a vacuum at 40°C until constant weight to obtain the purified product (30.77 g; 46.2 percent; HPLC purity: 99.5 percent).To an ice-cooled suspension of commercially available compound6a (1.66 g, 10.0 mmol) in 50 mL of DCM was added N, Ndiisopropylethylamine(3.53 mL, 20.0 mmol), then MOMCl(2.30 mL, 30.0 mmol) was added dropwise. The reaction was graduallyallowed to reach room temperature and was stirred for 6 h.Then, the mixture was quenched with saturated ammonium chloridesolution (20 mL) and was extracted with DCM. The organiclayers were combined, dried over sodium sulfate, filtered, andevaporated. The brownish residue was purified over silica gel toobtain a colorless oil (1.11 g, 53percent). 1H NMR (400 MHz, CDCl3) d7.77 (s, 1H), 7.66 (d, J = 8.5 Hz, 1H), 6.93 (d, J = 8.5 Hz, 1H), 5.29(s, 2H), 3.96 (s, 3H), 3.54 (s, 3H), 2.57 (s, 3H). ESI-MS m/z: 211.1[M+H]+.General procedure: Step 1: [068] To a stirred solution of 10.0 g (60.2 mmol) of 1-(4-hydroxy-3-methoxyphenyl)ethan-1 -one in 200 ml. of DMF were added 12.5 g (90.5 mmol) of K2CO3 and 1 1.3 g (66.07 mmol) of benzyl bromide. The reaction mixture was stirred at 40 °C for 1 h under N2 atmosphere. It was diluted with 500 ml. of water, and filtered; the filter cake was washed with water to obtain compound 1-1 , which was used in the next step without further purification. LC-MS: m/e = 257 [M+H]+.

Isoacetovanillone is a volatile compound isolated from oak wood. Also a byproduct in the production of Acetovanillone.

Molecular Weight:166.17
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:166.062994177
Monoisotopic Mass:166.062994177
Topological Polar Surface Area:46.5
Heavy Atom Count:12
Complexity:167
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes