Sodium borohydride → 7-Bromo-1,2,3,4-tetrahydro-3,3-dimethyl-1-naphthalenol

HRID 2292041Notes

Reaction equation

HRID 2292041 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][C:7]([CH3:14])([CH3:13])[CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][C:7]([CH3:14])([CH3:13])[CH2:8][CH:9]2[OH:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 157119867-broMo-3,3-diMethyl-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 148194057-Bromo-1,2,3,4-tetrahydro-3,3-dimethyl-1-naphthalenolYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7-bromo-3,3-dimethyl-3,4-dihydro-1(2H)-naphthalenone (7.8 g) in dry ethanol (50 ml) at 0° C., was treated with sodium borohydride (1.5 g). The mixture was stirred and allowed to warm to room temperature over 18 hours, and the ethanol removed in vacuo. The residue was partitioned between ethyl acetate and water, and the organic layers were dried and evaporated to give the alcohol as a gum (7.0 g)

Workup

  1. customthe ethanol removed in vacuo
  2. customThe residue was partitioned between ethyl acetate and water
  3. customthe organic layers were dried
  4. customevaporated

Sources & evidence

ORD record
ord-967ecdb79aab45dca56c6e3262654798
Source dataset
uspto-grants-1989_01
Patent number
US04800212

Reaction notes

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