2-Phenylethanol → 3,4-Difluorocinnamic acid beta-phenylethyl ester

HRID 976034Notes

Reaction equation

HRID 976034 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[F:13])[CH:5]=[CH:6][C:7]([OH:9])=[O:8].[C:14]1([CH2:20][CH2:21]O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:14]1([CH2:20][CH2:21][O:8][C:7](=[O:9])[CH:6]=[CH:5][C:4]2[CH:10]=[CH:11][C:12]([F:13])=[C:2]([F:1])[CH:3]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 60542-PhenylethanolHCID 1454863-(3,4-Difluorophenyl)prop-2-enoic acid

Product 1

HCID 3831453,4-Difluorocinnamic acid beta-phenylethyl esterYield 38%

Procedure

Reaction of 3,4-difluorocinnamic acid and β-phenylethyl alcohol as outlined in method A provided 67J-17-A as snow-white crystals (38% yield): mp 53°-57° C., 1H NMR (CDCl3) δ:7,49 (d, 1H, J=16 Hz), 7.30-7.05 (m, 8H) 6.27 (d, 1H, J=16 Hz), 4.36 (t, 2H, J=7.0 Hz), 3.82 (s, 3H), 2.95 (t, 2H, J=7.0 Hz); FABMS (NBA, +VE m/z 289 (M+H). Anal. (C17H14O2F2) C,H.

Sources & evidence

ORD record
ord-5728525cee514d29ba9d012ca8892412
Source dataset
uspto-grants-1997_03
Patent number
US05610185

Reaction notes

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