Sodium Hydroxide → 3-{[3-(Methyloxy)phenyl]methyl}hexanoic acid

HRID 1992879Notes

Reaction equation

HRID 1992879 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([CH2:17][CH2:18][CH3:19])[CH2:11][C:12]([O:14]CC)=[O:13])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+]>C1COCC1.CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([CH2:17][CH2:18][CH3:19])[CH2:11][C:12]([OH:14])=[O:13])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68534653HCID 68534653, compound

Product 1

HCID 685385143-{[3-(Methyloxy)phenyl]methyl}hexanoic acidYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl ester 91 (3.12 g, 11.8 mmol) was saponified with 1 N NaOH in THF and EtOH to give 2.76 g (99%) of the title compound (92) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 0.87 (t, J=6.8 Hz, 3H), 1.25-1.45 (m, 4H), 2.10-2.22 (m, 1H), 2.25-2.30 (m, 2H), 2.50-2.60 (m, 1H), 2.65-2.75 (m, 1H), 3.79 (s, 3H), 6.70-6.80 (m, 3H), 7.19 (d, J=7.8 Hz, 1H).

Sources & evidence

ORD record
ord-1a3cab2923534b20b2ab52c5d2c44f50
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

Loading…