Hydrochloric Acid → 2-(4-phenylbenzyloxy)-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid

HRID 1169326Notes

Reaction equation

[C:1]1([C:7]2[CH:29]=[CH:28][C:10]([CH2:11][O:12][C:13]3[CH:14]=[CH:15][C:16]4[CH2:22][CH2:21][CH2:20][C:19]([C:23]([O:25]C)=[O:24])=[CH:18][C:17]=4[CH:27]=3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CO.C1COCC1>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][O:12][C:13]3[CH:14]=[CH:15][C:16]4[CH2:22][CH2:21][CH2:20][C:19]([C:23]([OH:25])=[O:24])=[CH:18][C:17]=4[CH:27]=3)=[CH:28][CH:29]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To methyl 2-(4-phenylbenzyloxy)-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (1.22 g, 3.17 mmol) dissolved in a mixed solvent of methanol (20 ml) and THF (35 ml) was added a 1N aqueous solution of sodium hydroxide (10 ml), and the resulting mixture was stirred at room temperature for 18 hours and 60° C. for 2 hours. The reaction mixture was mixed with 1 N hydrochloric acid (12 ml) at room temperature, was concentrated under reduced pressure and was mixed with water, and an insoluble material was collected by filtration. The insoluble material was washed successively with water and hexane, and was dried under reduced pressure to obtain 2-(4-phenylbenzyloxy)-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid (1.38 g).

Workup

concentrationwas concentrated under reduced pressure
additionwas mixed with water
filtrationan insoluble material was collected by filtration
washThe insoluble material was washed successively with water and hexane
customwas dried under reduced pressure

Sources & evidence

ORD record: ord-825508ac58c4459997b092f9f123e638
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06627651B1

Reaction notes

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