7-Bromo-1,2,3,4-tetrahydronaphthalen-1-one → 7-Bromo-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 1431955Notes

Reaction equation

HRID 1431955 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][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][CH2:7][CH2:8][CH:9]2[OH:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2527317-Bromo-1,2,3,4-tetrahydronaphthalen-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 126949197-Bromo-1,2,3,4-tetrahydronaphthalen-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 9.5 g of 7-bromo-3,4-dihydronaphthalen-1(2H)-one (42 mmol), prepared according to the method described in Synth. Comm. 1994, 2777, dissolved in 100 ml of ethanol, there are added, at 0° C. and in two portions, 0.8 g of sodium borohydride (21 mmol). The reaction mixture is then allowed to come back up to ambient temperature over 30 minutes, and then the ethanol is evaporated off. The residue is taken up in 100 ml of toluene and 100 ml of water. After separation, the aqueous phase is extracted with 50 ml of toluene. The toluene phases are combined, washed with a saturated aqueous solution of sodium chloride and are then evaporated to yield 7-bromo-1,2,3,4-tetrahydronaphth-1-ol in the form of an oil.

Workup

  1. customthe ethanol is evaporated off
  2. customAfter separation
  3. extractionthe aqueous phase is extracted with 50 ml of toluene
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. customare then evaporated

Sources & evidence

ORD record
ord-df159afcdd424af68f07d2d3b95ee1e7
Source dataset
uspto-grants-2009_11
Patent number
US07612061B2

Reaction notes

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