Sodium Acetate → 3-(2-Methylbenzoyl)-5,6,7,8-tetrahydro-2-naphthol

HRID 36937Notes

Reaction equation

HRID 36937 reaction equation
Br[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[C:3]=1[OH:21].C([O-])(=O)C.[Na+]>[Pd].CO>[CH3:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]([C:4]1[C:3]([OH:21])=[CH:2][C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=1)=[O:20]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 100204261-Bromo-3-(2-methylbenzoyl)-5,6,7,8-tetrahydro-2-naphthol

Product 1

HCID 103782473-(2-Methylbenzoyl)-5,6,7,8-tetrahydro-2-naphtholYield 96.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-bromo-3-(2-methylbenzoyl)-5,6,7,8-tetrahydro-2-naphthol (3.33 g), sodium acetate (0.82 g), 5% palladium-on-carbon (50% hydrate, 1.0 g) and methanol (10 ml) was subjected to catalytic reduction. After the theoretical amount of hydrogen had been absorbed, the catalyst was filtered off. The solvent was then distilled off and the residue was diluted with water and extracted with ethyl acetate. The extract was washed with water and dried (MgSO4) and the solvent was distilled off to give 3-(2-methylbenzoyl)-5,6,7,8-tetrahydro-2-naphthol as an oil (2.45 g, 96.5%).

Workup

  1. customAfter the theoretical amount of hydrogen had been absorbed
  2. filtrationthe catalyst was filtered off
  3. distillationThe solvent was then distilled off
  4. additionthe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried (MgSO4)
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-19b17b6c1f674e2c8896c8981d492d84
Source dataset
uspto-grants-1995_05
Patent number
US05418239

Reaction notes

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