Methanol → 5-Hydroxy-1-tetralone

HRID 1608046Notes

Reaction equation

HRID 1608046 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:13].B(Br)(Br)Br.CO>C(Cl)Cl>[OH:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 366205-Methoxytetralone

Product 1

HCID 1199215-Hydroxy-1-tetralone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

1 mol of 5-methoxy-1-tetralone are dissolved in 5 l of methylene chloride and the solution is cooled to -78° C. 500 ml of boron tribromide in 2.3 1 of methylene chloride are added dropwise to this solution. The mixture is stirred at -78° C. for 30 minutes and then at 0° C. for 2.5 hours and cooled again to -78° and 3 l of methanol are slowly added dropwise. The mixture is evaporated, the residue is taken up in methylene chloride and the mixture is extracted 3 times with 10% strength sodium hydroxide solution. The combined sodium hydroxide solutions are acidified with concentrated hydrochloric acid and extracted 3 times by shaking with methylene chloride. After drying over sodium sulphate, the extract is evaporated. The residue is pure product and does not need to be recrystallized. The melting point is 210°-215° C.

Workup

  1. waitat 0° C. for 2.5 hours
  2. temperaturecooled again to -78°
  3. customThe mixture is evaporated
  4. extractionthe mixture is extracted 3 times with 10% strength sodium hydroxide solution
  5. extractionextracted 3 times
  6. stirringby shaking with methylene chloride
  7. dry with materialAfter drying over sodium sulphate
  8. customthe extract is evaporated
  9. customto be recrystallized

Sources & evidence

ORD record
ord-28879cb88919427db11a53cb0541fd18
Source dataset
uspto-grants-1989_09
Patent number
US04868332

Reaction notes

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