Hydrochloric Acid → 2-(4-methylbenzyloxy)-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid
Reaction equation
[CH3:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]3[CH2:17][CH2:16][CH2:15][C:14]([C:18]([O:20]C)=[O:19])=[CH:13][C:12]=3[CH:22]=2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO.C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]3[CH2:17][CH2:16][CH2:15][C:14]([C:18]([OH:20])=[O:19])=[CH:13][C:12]=3[CH:22]=2)=[CH:23][CH:24]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To methyl 2-(4-methylbenzyloxy)-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (2.34 g, 7.26 mmol) dissolved in a mixed solvent of methanol (25 ml) and THF (25 ml) was added a 1N aqueous solution of sodium hydroxide (23 ml), and the resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was mixed with 1 N hydrochloric acid (23 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-methylbenzyloxy)-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid (2.11 g, 6.84 mmol, 94%).
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-ee8a47a5c0ef4dd1a24b03978b30a36f
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06627651B1
Reaction notes
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