Dichloromethane → 6-methylnaphthalen-2-ol

HRID 1290495Notes

Reaction equation

HRID 1290495 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 6344DichloromethaneHCID 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 dichloromethanie (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 (2x500 ml). The organic extracts were combined, dried (MgSO4) and evaporated to give a solid. Purification by flash column chromatography on silica, eluting with ethyl acctate/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 (2x500 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 acctate/hexane (5:95 v/v)

Sources & evidence

ORD record
ord-0f07effdf83b4931b731eaf7d379dbfb
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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