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

HRID 1871293Notes

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 title compound. 1H NMR (DMSO-d6) δ 3.15 (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-5f1d736aa21a451a97387c13280603b5
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06103708

Reaction notes

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