Hydrochloric Acid → 4-(n-Pentoxyphenyl)-4'-carboxybiphenyl

HRID 1736291Notes

Reaction equation

[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27]C)=[O:26])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[Na+].Cl>O1CCCC1>[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-(n-pentyloxyphenyl)-4'-methoxycarbonylbiphenyl (220 mg, 0.58 mmol) and 5N sodium hydroxide (1.17 mL, 5.88 mmol) in tetrahydrofuran (20 mL) was heated at 80° C. under reflux for a period of 18 h. The cooled mixture was acidified with 1N hydrochloric acid (35 mL) and partitioned between ethyl acetate and water. The organic suspension was washed with water (3×) and brine. The organic layer was then filtered to give the carboxylic acid, 4-(n-pentyloxyphenyl)-4'-carboxybiphenyl (210 mg).

Workup

temperatureunder reflux for a period of 18 h
custompartitioned between ethyl acetate and water
washThe organic suspension was washed with water (3×) and brine
filtrationThe organic layer was then filtered

Sources & evidence

ORD record: ord-ea850ea30c1c4822a3629dcab13ea1d7
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05541160

Reaction notes

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