Sodium Hydroxide → 6,6,6-Trifluoro-3-{[3-(methyloxy)phenyl]methyl}hexanoic acid

HRID 1992901Notes

Reaction equation

HRID 1992901 reaction equation
[F:1][C:2]([F:22])([F:21])[CH2:3][CH2:4][CH:5]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[CH2:6][C:7]([O:9]CC)=[O:8].[OH-].[Na+]>C1COCC1.CCO>[F:1][C:2]([F:21])([F:22])[CH2:3][CH2:4][CH:5]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[CH2:6][C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68537268Ethyl 6,6,6-trifluoro-3-{[3-(methyloxy)phenyl]methyl}hexanoate

Product 1

HCID 685398486,6,6-Trifluoro-3-{[3-(methyloxy)phenyl]methyl}hexanoic acidYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl ester (119) (1.75 g, 5.50 mmol) was saponified with 1 N NaOH in THF and EtOH to give 1.56 g (98%) of the title compound (120) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 1.60-1.70 (m, 2H), 2.05-2.40 (m, 5H), 2.55-2.70 (m, 2H), 3.80 (s, 3H), 6.70-6.74 (m, 1H), 6.74-6.80 (m, 2H), 7.21 (t, J=7.9 Hz, 1H).

Sources & evidence

ORD record
ord-90be3f3a830a4f70bc4f6958a1007aad
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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