Water → 2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid

HRID 400742Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([O:12]C)=[O:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20].[OH-].[Na+].O>CCO>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 2-(methoxymethyl)-2′-methylbiphenyl-4-carboxylate obtained in step 3 (40 g; 147.97 mmol) in EtOH (1200 mL) was added NaOH (88.78 mL; 5 M; 443.90 mmol) after which the mixture was heated at 60° C. for one hour. Reaction mixture was cooled to room temperature and concentrated under vacuum to give a yellow solid. Water was added and the aqueous phase was washed with EtOAc. The aqueous phase was then acidified with HCl (1 M) and extracted with EtOAc to give the title compound as a yellow solid (35.1 g, 92%). 1H NMR (DMSO-d6) δ 12.99 (br s, 1H), 8.09 (s, 1H), 7.92-7.89 (m, 1H), 7.33-7.22 (m, 4H), 7.10-7.08 (m, 1H), 4.11 (m, 2H), 3.18 (s, 3H), 1.99 (s, 3H). HPLC (Method A) Rt 4.52 min (Purity: 96.4%). LC/MS (Method B): 255.2 (M−H)−.

Workup

customReaction mixture
temperaturewas cooled to room temperature
concentrationconcentrated under vacuum
customto give a yellow solid
washthe aqueous phase was washed with EtOAc
extractionextracted with EtOAc

Sources & evidence

ORD record: ord-6395ceaf6725416c83ae6143f3a7a53d
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741923B2

Reaction notes

Loading…