Dichloromethane → 6-methylnaphthalen-2-ol

HRID 864803Notes

Reaction equation

HRID 864803 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](C)=[CH:8][CH:7]=[CH:6]2.B(Br)(Br)Br.Cl[CH2:19]Cl>>[CH3:19][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[CH:4]=[C:3]([OH:2])[CH:12]=[CH:11]2

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 25134Boron tribromideHCID 102196186-methoxy-1-methylnaphthalene

Product 1

HCID 2428346-methylnaphthalen-2-ol

Conditions

Temperature
-60 °C

Procedure

To a solution of 6-methoxy-1-methylnaphthalene (6.4 g) in dichloromethane (500 ml), cooled to -60° C., was added boron tribromide (45 ml of a 1M solution in dichloromethane). The resulting mixture was stirred at -60° C. for 3 hours. The reaction was quenched with water (500 ml) and extracted with dichloromethane (2×500 ml). The organic extracts were combined, dried (MgSO4) and evaporated to give a solid. Purification by flash column chromatography on silica, eluting with ethyl acetate/hexane (5:95 v/v) gave 6-methyl-2-naphthol (3.76 g) as a white solid. This was used without further characterisation.

Workup

  1. customThe reaction was quenched with water (500 ml)
  2. extractionextracted with dichloromethane (2×500 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a solid
  6. customPurification by flash column chromatography on silica
  7. washeluting with ethyl acetate/hexane (5:95 v/v)

Sources & evidence

ORD record
ord-58ac14536bfe4f5eb37959a3810ac1c4
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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