
Methyl3-(4-hydroxyphenyl)hex-4-ynoate synthesis
- Product Name:Methyl3-(4-hydroxyphenyl)hex-4-ynoate
- CAS Number:865234-02-2
- Molecular formula:C13H14O3
- Molecular Weight:218.25

865233-34-7

74-88-4

865234-02-2
3-(4-Hydroxyphenyl)hex-4-ynoic acid (23.5 g, 115 mmol) was dissolved in acetone (230 mL) and potassium bicarbonate (11.5 g, 115 mmol) was added and stirred for 15 minutes. Subsequently, iodomethane (5 mL, 80 mmol) was added and the reaction mixture was stirred at 40 °C overnight. Iodomethane (3 mL, 48 mmol) was added again and the reaction continued to be heated for 24 hours. After completion of the reaction, the insoluble material was removed by filtration and washed with acetone. The filtrate was concentrated to an oil and purified by silica gel column chromatography using a dichloromethane solution containing 2.5% methanol as eluent. Methyl 3-(4-hydroxyphenyl)hex-4-ynoate (21.5 g, 85% yield) was finally obtained as a light yellow oil.1H NMR (500 MHz, acetone-d6) δ: 8.2 (br s, 1H), 7.20 (d, J=9.5 Hz, 2H), 6.77 (d, J=9.0 Hz, 2H), 3.98 (m, 1H), 3.60 (s, 3H), 2.65 (m, 2H), 1.78 (d, J=2.5Hz, 3H).MS (ESI) m/e: 219.1 (M+H)+, 241 (M+Na)+.
Yield:865234-02-2 90.9%
Reaction Conditions:
with methanesulfonic acid at 65; for 2 h;
Steps:
85
Intermediate 115: Methyl 3-(4-hydroxyphenyl) hex-4-ynoateTo a 250 mL RB flask fitted with magnetic stirrer was charged with methanol (10 mL). To the stirred solvent was added 3-(4-Hydroxyphenyl) hex-4-ynoic acid (0.62 g, 20.14 mmol) and methane sulfonic acid (3 mL), it was heated at 65 for 2 h. The RM was concentrated, extracted with ethyl acetate (50 mL X 2). The organic layer was washed with water (50 mL) and saturated brine solution (50 mL). The organic layer was dried over anhydrous Na2S04 and the solvent was removed under reduced pressure to obtain the product. (0.4 g, yield: 90.9%).
References:
WO2012/11125,2012,A1 Location in patent:Page/Page column 151; 153
![(+/-)-5-[1-(4-hydroxy-phenyl)-but-2-ynyl]-2,2-dimethyl-[1,3]dioxane-4,6-dione](/CAS/20180629/GIF/865233-33-6.gif)
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