HCID 13317769, compound → HCID 19767569, compound

HRID 1590557Notes

Reaction equation

HRID 1590557 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[C:10]([O:12]C)=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1>ClCCl.[B]>[CH3:1][C:2]1([CH3:14])[C:11]2[C:10]([OH:12])=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 13317769HCID 13317769, compound

Product 1

HCID 19767569HCID 19767569, compoundYield 73.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 5462311BoronSolvent

Procedure

To a solution of 8,8-dimethyl-1-methoxy-5,6,7,8-tetrahydronaphthalene (16.4 g, 86 mmole) in dry dichloromethane (300 ml), boron tribomide (23.75 g, 91 mmole) was added at -58°. The mixture was stirred and warmed to 0° over 3 hours, poured into ice-water (1 lit) and extracted with diethylether. The ethereal extract was washed with water and aqueous saturated sodium chloride, dried and evaporated. The residue was chromatographed in silica gel using dichloromethane as eluant to give 8,8-dimethyl-5,6,7,8-tetrahydro-1-naphthol as an oil (11.2 g, 73.2%).

Workup

  1. temperaturewarmed to 0° over 3 hours
  2. extractionextracted with diethylether
  3. extractionThe ethereal extract
  4. washwas washed with water and aqueous saturated sodium chloride
  5. customdried
  6. customevaporated
  7. customThe residue was chromatographed in silica gel

Sources & evidence

ORD record
ord-0e660819c8c54971b62da10a0e428322
Source dataset
uspto-grants-1993_04
Patent number
US05204336

Reaction notes

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