Water → 1,2,2a,3,4,5-Hexahydroacenaphthylen-1-ol

HRID 331224Notes

Reaction equation

HRID 331224 reaction equation
[C:1]1(=[O:13])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1.[BH4-].[Na+].O>CO>[CH:1]1([OH:13])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 128585822a,3,4,5-Tetrahydro-1(2H)-acenaphthylenone

Product 1

HCID 2652581,2,2a,3,4,5-Hexahydroacenaphthylen-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2a,3,4,5-Tetrahydro-2H-acenaphthylen-1-one (4.85 g) was dissolved in methanol (70 ml). Sodium borohydride (1.07 g) was added to the solution under ice-cooling, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over magnesium sulfate, and concentrated to give 2a,3,4,5-tetrahydro-2H-acenaphthylen-1-ol.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cb3f040aaf2d4d52aeaa7a6e7014f502
Source dataset
uspto-grants-2014_11
Patent number
US08877779B2

Reaction notes

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