Cornforth reagent → 2-Acetyl-8,8-dimethyl-5,6,7,8-tetrahydronaphthalene

HRID 484372Notes

Reaction equation

HRID 484372 reaction equation
[OH:1][CH:2]([C:4]1[CH:13]=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][C:7]([CH3:15])([CH3:14])[C:6]=2[CH:5]=1)[CH3:3].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.FC(F)(F)C([O-])=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[C:2]([C:4]1[CH:13]=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][C:7]([CH3:15])([CH3:14])[C:6]=2[CH:5]=1)(=[O:1])[CH3:3]

Participants

5

Reactant 3

HCID 2724130Cornforth reagentHCID 9813011pyridine TFAHCID 197480192-(1-Hydroxyethyl)-8,8-dimethyl-5,6,7,8-tetrahydronaphthalene

Product 1

HCID 197480082-Acetyl-8,8-dimethyl-5,6,7,8-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2.44 g (11.96 mmol) of 2-(1-hydroxyethyl)-8,8-dimethyl-5,6,7,8-tetrahydronaphthalene in 35 ml of methylene chloride was added 6.75 g (17.9 mmol) of pyridinium dichromate and 330 mg (1.68 mmol) of pyridinium trifluoroacetate. The mixture was stirred at room temperature for 24 h and then diluted with 35 ml of low-boiling petroleum ether. The mixture was filtered through a short column of anhydrous MgSO4 and silica and the filtrate then concentrated in-vacuo to give the title compound as a colorless oil. PMR (CDCl3): δ 1.30 (6H, s), 1.60-1.70 (2H, m), 1.72-1.84 (2H, m), 2.56 (3H, s), 2.78 (2H, t, J~6.1 Hz), 7.08 (1H, d, J~7.8 Hz), 7.61 (1H, dd, J~7.8 Hz, 1.9 Hz), 7.93 (1H, d, J~1.9 Hz).

Workup

  1. filtrationThe mixture was filtered through a short column of anhydrous MgSO4 and silica
  2. concentrationthe filtrate then concentrated in-vacuo

Sources & evidence

ORD record
ord-8bc28512ad2246d2a108133fea62cacb
Source dataset
uspto-grants-1993_07
Patent number
US05231113

Reaction notes

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