Potassium Hydroxide → 2'-Methoxy-[1,1';3',1"]terphenyl-5'-carboxylic acid

HRID 1841304Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:8]([O:17][CH3:18])=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:10]=1)=[O:4].[OH-].[K+]>C1COCC1.CCOCC>[CH3:18][O:17][C:8]1[C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

At ambient temperature, to a stirred solution of 2′-methoxy-[1,1′;3′,1″]terphenyl-5′-carboxylic acid methyl ester (1.148 g, 3.606 mmol) in THF (36.06 mL) was added 1N KOH (36.06 mL) and the reaction was stirred for 16 h. The reaction was heated at 100° C. for an additional 24 h. The reaction was cooled to ambient temperature, diluted with ether (100 mL) and extracted with 0.1N NaOH. The aqueous extracts were washed with ether (3×), acidified with 6N HCl and extracted with EtOAc. The organic extracts were dried (MgSO4) and concentrated to give 1.043 g (95%) of the tide compound. 1H NMR (DMSO-d6) δ3.15 (s, 3 H), 7.40-7.52 (m, 6 H), 7.58-7.60 (m, 4 H), 7.88 (s, 2 H), 13.04 (s, 1 H).

Workup

temperatureThe reaction was cooled to ambient temperature
extractionextracted with 0.1N NaOH
washThe aqueous extracts were washed with ether (3×)
extractionextracted with EtOAc
dry with materialThe organic extracts were dried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-dbd95dc4f2cd4f6e8b4f257d92b8cbc8
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06683107B2

Reaction notes

Loading…