Sodium Hydroxide → HCID 68533199, compound

HRID 2108663Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:31])[C:11]=1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[C:15]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH:14]=1)[C:5]([O:7]C)=[O:6].[OH-].[Na+]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:31])[C:11]=1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[C:15]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH:14]=1)[C:5]([OH:7])=[O:6]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirring solution of afford methyl 3,5-dimethyl-4-[3′-(4-fluorobenzyl)-4′-methoxymethoxybenzyl]benzoate (compound 78, step f, 2.8 g, 6.63 mmol) in MeOH (80 mL) at 0° C. was added NaOH (27 mL, 1 N). After heating at 50° C. for 16 h, the solvent was removed under reduced pressure and the residue was acidified with 1 N HCl to pH=1, and the mixture was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to afford 3,5-dimethyl-4-[3′-(4-fluorobenzyl)-4′-methoxymethoxybenzyl]benzoic acid as white solid (2.7 g, 100%): 1H NMR (300 MHz, DMSO-d6): 12.71 (s, 1H), 7.64 (s, 2H), 7.01-7.22 (m, 4H), 6.95 (d, J=8.4 Hz, 1H), 6.85 (d, J=2.1 Hz, 1H), 6.73 (dd, J=2.1, 8.4 Hz, 1H), 5.15 (s, 2H), 3.98 (s, 2H), 3.86 (s, 2H), 3.27 (s, 3H), 2.25 (s, 6H).

Workup

customthe solvent was removed under reduced pressure
extractionthe mixture was extracted with EtOAc
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-61d478ec8ad44f11a5616a7d3293de76
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514419B2

Reaction notes

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