Hydrochloric Acid → 2-benzyloxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid

HRID 1169318Notes

Reaction equation

HRID 1169318 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:18][CH2:17][CH2:16][C:15]([C:19]([O:21]C)=[O:20])=[CH:14][C:13]=2[CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O1CCCC1.Cl>CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:18][CH2:17][CH2:16][C:15]([C:19]([OH:21])=[O:20])=[CH:14][C:13]=2[CH:23]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22989957methyl 2-benzyloxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate

Product 1

HCID 229901982-benzyloxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acidYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methyl 2-benzyloxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (2.28 g, 7.39 mmol) suspended in methanol (25 ml) was added a 1N aqueous solution of sodium hydroxide (23 ml), and the resulting mixture was stirred at room temperature for 13 hours. In order to complete the reaction, tetrahydrofuran (25 ml) was added, and the resulting mixture was stirred at 60° C. for 2 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 with water and was dried under reduced pressure to obtain 2-benzyloxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid (2.09 g, 7.10 mmol, 96%).

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred at 60° C. for 2 hours
  3. concentrationwas concentrated under reduced pressure
  4. additionwas mixed with water
  5. filtrationan insoluble material was collected by filtration
  6. washThe insoluble material was washed with water
  7. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-3da095211e4a40f782693e8fae59e077
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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