Sodium Hydroxide → HCID 22620575, compound

HRID 840973Notes

Reaction equation

HRID 840973 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[C:14]2[CH2:13][CH2:12][CH2:11][C:10]([C:15]([O:17]C)=[O:16])=[C:9]([CH3:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1>CO>[CH3:3][C:4]1[C:14]2[CH2:13][CH2:12][CH2:11][C:10]([C:15]([OH:17])=[O:16])=[C:9]([CH3:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22620571HCID 22620571, compound

Product 1

HCID 22620575HCID 22620575, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2N-aqueous sodium hydroxide solution (10 ml) was added to a solution of methyl 4,9-dimethyl-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (0.85 g, 3.68 mmol) in methanol (10 ml), and the mixture was heated under reflux for 3 hours. The methanol was distilled off under reduced pressure and the residue was adjusted to pH 1 to 2 with 4N-hydrochloric acid and then extracted three times with ethyl acetate. The extract solution was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the thus obtained solid was washed with n-hexane to obtain 0.56 g of 4,9-dimethyl-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. distillationThe methanol was distilled off under reduced pressure
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe extract solution was dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. washthe thus obtained solid was washed with n-hexane

Sources & evidence

ORD record
ord-51e7a809b26b431d8096c235862ddc36
Source dataset
uspto-grants-2002_04
Patent number
US06369110B1

Reaction notes

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