Water → 2-Benzyloxy-[1,1';2',1'']terphenyl-3''-carboxylic acid

HRID 269538Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:9]=[CH:10][CH:11]=1)=[O:5])C.[OH-].[Na+].O>C(O)C>[CH2:25]([O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:13]1[C:12]([C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=2)=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 50 °C

Procedure

2-Benzyloxy-[1,1′;2′,1″]terphenyl-3″-carboxylic acid ethyl ester (84 mg, 0.206 mmol) was dissolved in ethanol (2 ml) and 2M sodium hydroxide (0.5 ml) added. The mixture was stirred and heated to 50° C. for 4 h. Water was added and the mixture extracted with isohexane. The aqueous layer was acidified with 2M hydrochloric acid and extracted with diethyl ether (2×10 ml). The combined organic phases were washed with water, dried (MgSO4) and evaporated. The oil was triturated with isohexane and the resulting white solid filtered, washed with isohexane and dried in vacuo. (42 mg, 54%).

Workup

extractionthe mixture extracted with isohexane
extractionextracted with diethyl ether (2×10 ml)
washThe combined organic phases were washed with water
dry with materialdried (MgSO4)
customevaporated
customThe oil was triturated with isohexane
filtrationthe resulting white solid filtered
washwashed with isohexane
customdried in vacuo

Sources & evidence

ORD record: ord-d92563337723441e9c318ae746aa1691
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446222B2

Reaction notes

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