Methanol → 4-(3-Hydroxypropoxy)-3-methyl-benzoic acid
Reaction equation
F[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1C#CCOC)[C:5]([O:7]C)=[O:6].[CH2:17]1C[O:20][CH2:19][CH2:18]1.[OH-:22].[Na+].[CH3:24]O>>[OH:20][CH2:19][CH2:18][CH2:17][O:22][C:11]1[CH:10]=[CH:9][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[CH3:24]Participants
Procedure
To methyl 3-fluoro-4-(3-methoxyprop-1-ynyl)benzoate (1.4 g, 6.3 mmol) in 2:1 mixture of THF:MeOH (15 mL) at room temperature was added 4 M sodium hydroxide solution (1.9 mL, 7.56 mmol) and reaction mixture was stirred for 1 hour. The solvent was removed in vacuo and the reaction mixture was extracted with ethyl ether, and layers were separated. The aqueous layer was acidified with 1M HCl solution and extracted with ethyl ether. The organics were separated, dried and concentrated in vacuo to give 4-(3-hydroxypropoxy)-3-methyl-benzoic acid (1.1 g, 85%) as a white solid. ESI-MS m/z calc. 208.2. found 209.2 (M+1)+; Retention time: 1.22 minutes (3 min run); 1H NMR (400 MHz, CDCl3) δ 7.85 (dd, J=8.0, 1.4 Hz, 1H), 7.80 (dd, J=9.5, 1.3 Hz, 1H), 7.59-7.49 (m, 1H), 4.39 (s, 2H), 3.48 (s, 3H).
Workup
- customThe solvent was removed in vacuo
- extractionthe reaction mixture was extracted with ethyl ether, and layers
- customwere separated
- extractionextracted with ethyl ether
- customThe organics were separated
- customdried
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-2cbedcfd519e40c598abc7a511f208c0
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181273B2
Reaction notes
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