Hydrochloric Acid → 2-Propenoic acid, 3-[4-(acetyloxy)-3-methoxyphenyl]-
Reaction equation
[C:1]([OH:14])(=[O:13])/[CH:2]=[CH:3]/[C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1.C(N(CC)CC)C.[C:22](OC(=O)C)(=[O:24])[CH3:23].Cl>C1COCC1.CN(C1C=CN=CC=1)C>[C:22]([O:10][C:9]1[CH:11]=[CH:12][C:4](/[CH:3]=[CH:2]/[C:1]([OH:14])=[O:13])=[CH:5][C:6]=1[O:7][CH3:8])(=[O:24])[CH3:23]Participants
Procedure
Ferulic acid (10 g, 51 mmol) is solubilised in 100 ml of anhydrous THF under argon. Triethylamine (8.7 ml, 61 mmol, 1.2 eq) is added quickly, then DMAP (3.34 g, 27 mmol, 0.5 eq) at ambient temperature and under argon. Finally acetic anhydride (5.9 mL, 61 mmol, 1.2 eq) is added in 3 min, at ambient temperature. This is kept whilst stirring, at ambient temperature, for 18 h, then the medium is transferred into a separation funnel. This medium is diluted with 100 ml of THF, acidified with 40 ml of HCl 5% v/v and the organic phase is washed with 5×40 ml of H2O. The final organic phase is dried over MgSO4, filtered, then evaporated dry in a rotary evaporator (40° C., 30 mbar). 9.5 g of a crude yellow solid are obtained with a crude yield of 79% and a molar purity measured by NMR of 86%. The product is involved in the following step without purification.
Workup
- customat ambient temperature
- customthe medium is transferred into a separation funnel
- washthe organic phase is washed with 5×40 ml of H2O
- dry with materialThe final organic phase is dried over MgSO4
- filtrationfiltered
- customevaporated
- customdry in a rotary evaporator (40° C., 30 mbar)
Sources & evidence
- ORD record
- ord-6b2628d656c84552b06ed062674ad71f
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067908B2
Reaction notes
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