Sodium Hydroxide → HCID 22620564, compound

HRID 840972Notes

Reaction equation

HRID 840972 reaction equation
[CH3:1][C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][CH2:4][C:3]=1[C:13]([O:15]CC)=[O:14].[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][CH2:4][C:3]=1[C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22620521HCID 22620521, compound

Product 1

HCID 22620564HCID 22620564, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl 9-methyl-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (0.70 g, 3.04 mmol) was added to a mixture of a 2N aqueous sodium hydroxide solution and ethanol, and the resulting mixture was stirred at 70° C. for 5 hours. The reaction mixture was concentrated under reduced pressure and the resulting residue was dissolved in water and washed with ethyl acetate. The aqueous layer was acidified with 35% hydrochloric acid and extracted twice with diethyl ether, and the extract solution was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 0.33 g of 9-methyl-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in water
  3. washwashed with ethyl acetate
  4. extractionextracted twice with diethyl ether
  5. washthe extract solution was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5ec51774d706499982ee0124e3700bb1
Source dataset
uspto-grants-2002_04
Patent number
US06369110B1

Reaction notes

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