2′-Hydroxy-5′-methylacetophenone

yellow crystalline powder

Solid|Colourless to pale yellow solid; Sweet heavy-floral somewhat herbaceous aroma

2'-Hydroxy-5'-methylacetophenone is an aromatic ketone.

p-Tolyl acetate 2b (10 gm, 0.067 mol) was in 500 mL round bottom flask containing aluminium chloride (10.7 gm, 0.08 mol). It was heated on an oil bath at 140-150 °C for 5-6 hr. The progress of the reaction was monitored by TLC using ethyl acetate:hexane as a solvent system. The reaction mixture was quenched with crushed ice and obtained solid product was extracted with ethyl acetate (2×50 mL). The organic extracts were washed with brine solution (2×15 mL) and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to afford the corresponding crude compounds. The obtained compound 3b was recrystallized using aq. ethanol. Yield 92percent. M.p. 45-48 °C.To a solution of p-cresol (15 g, 139 mmol) in acetic anhydride (37.5 mL) was added pyridine (1.13 mL).After 12 h of stirring at 25 °C, the volatiles were evaporated. The resulting oil was taken up in diethylether, washed with 10percent aqueous sodium bicarbonate twice and brine once, and dried and evaporated togive the acetate (20.85 g, quant. yield) which was used without further purification; 36g of acetoxytoluene was added to a four-necked flask, heated to 110 ° C with anhydrous aluminum trichloride (36.77 g, 0.28 mol). After the addition, the temperature was raised to 165 ° C. After 1 hour of stirring at the same temperature, 1 19mL of 4mol / L hydrochloric acid solution was stirred at 80-90 ° C for 1 hour, then cooled to room temperature and stirred for 3 hours. Toluene (12.5mL * 6) extraction six times the solvent was evaporated and dried in vacuo to give the product 2-acetyl-p-cresol 35.85gGeneral procedure: A mixture of allyl phenyl ethers 1 (1 mmol) and iodine (20 molpercent) in polyethylene glycol-400(10 mL) was stirred at room temperature for 25-30 minutes. The reaction mixture was poured incold solution of sodium thiosulphate and extracted by ethyl acetate. The combine organic layerwas dried over anhydrous Na2SO4 and evaporated under vacuum and purified by columnchromatography. The corresponding product was obtained in 86-96percent yield.

Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes|Flavoring Agents -> JECFA Flavorings Index

Molecular Weight:150.17
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:150.068079557
Monoisotopic Mass:150.068079557
Topological Polar Surface Area:37.3
Heavy Atom Count:11
Complexity:154
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes