Water → 4,4-Dimethyl-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 1654329Notes

Reaction equation

HRID 1654329 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1([CH3:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[CH2:6][CH2:5]1.O>CO.CO.C1(C)C=CC=CC=1>[CH3:3][C:4]1([CH3:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]([OH:14])[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 962WaterHCID 2365474,4-Dimethyl-3,4-dihydro-2H-naphthalen-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 126430324,4-Dimethyl-1,2,3,4-tetrahydronaphthalen-1-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21867641Toluene methanolSolvent

Procedure

To a stirred suspension of sodium borohydride (3.5 g, 93 mmoles) in dry methanol (50 ml) at 0° C. under a nitrogen atmosphere was added a solution of 4,4-dimethyl-1-tetralone (10 g, 57.4 mmoles) in dry methanol:toluene (1:3) dropwise over a 45 minute period. After this time the mixture was allowed to warm to room temperature, and then two volumes of water were added. After stirring for 1 hour, the organic layer was separated, dried over magnesium sulfate, filtered, and evaporated under reduced pressure to leave a light yellow oil. This was purified by silica gel column chromatrography eluting with ethyl acetate:hexane (1:9) to give 1,2,3,4-tetrahydro-4,4-dimethyl-1-naphthol as a colorless oil. (9.89 g, 98%).

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto leave a light yellow oil
  6. customThis was purified by silica gel column chromatrography
  7. washeluting with ethyl acetate:hexane (1:9)

Sources & evidence

ORD record
ord-6d5958372f364a479b617e768333c49e
Source dataset
uspto-grants-1995_04
Patent number
US05405851

Reaction notes

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