Acetic Anhydride → 7-Bromo-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1004894Notes

Reaction equation

HRID 1004894 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.[Br:32][C:33]1[CH:34]=C2[C:40](=[CH:41][CH:42]=1)[C:39]([CH3:44])([CH3:43])[CH2:38][CH2:37]C2>C1C=CC=CC=1.[O-2].[O-2].[O-2].[Cr+6]>[Br:32][C:33]1[CH:34]=[C:6]2[C:40]([C:39]([CH3:43])([CH3:44])[CH2:38][CH2:37][C:5]2=[O:7])=[CH:41][CH:42]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 105860636-Bromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene2×

Product 1

HCID 107533577-Bromo-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-one

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 241BenzeneSolvent

Procedure

To a cold mixture (0° C.) of 209 g (200 mmol) of chromium trioxide, 100 ml (1.06 mol) of acetic anhydride and 200 ml (3.5 mol) of acetic a 1 acid was added a solution of 10 g (41.8 mmol) of 6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene (Compound F) in 125 ml of benzene. The reaction mixture was stirred for 1 hour, quenched with ice cold water and extracted with Et2O (3×100 ml). The organic layer was dried over MgSO4, concentrated in vacuo, and purified by column chromatography (silica, 10% EtOAc-hexane) to give the title compound as a white solid.

Workup

  1. customquenched with ice cold water
  2. extractionextracted with Et2O (3×100 ml)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography (silica, 10% EtOAc-hexane)

Sources & evidence

ORD record
ord-73724f13e6024d4f8a07188f394a7ed8
Source dataset
uspto-grants-2000_04
Patent number
US06051731

Reaction notes

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