Benzyl Bromide → [6-(Benzyloxy)naphthalen-2-yl]methanol

HRID 48100Notes

Reaction equation

HRID 48100 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([OH:13])[CH:7]=[CH:6]2.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+]>[CH2:14]([O:13][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[CH:4]=[C:3]([CH2:2][OH:1])[CH:12]=[CH:11]2)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 113327606-(Hydroxymethyl)naphthalen-2-ol

Product 1

HCID 21976870[6-(Benzyloxy)naphthalen-2-yl]methanol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 10796Cesium carbonateSolvent

Procedure

To a solution of 6-hydroxy methyl-naphthalen-2-ol (16) (1 equi.) and benzyl bromide (2) (1 equi.) in DMF (3 mL/mmole), cesium carbonate (1.25 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h, quenched with water, extracted with ethyl acetate:hexane(1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (20% THF/hexanes) and recrystallization from EtOAc-Hexane (1:2) afforded (6-benzyloxy-naphthalen-2-yl)-methanol (17) a white solid (88%).

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate:hexane(1:1)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography
  7. customon silica gel (20% THF/hexanes) and recrystallization from EtOAc-Hexane (1:2)

Sources & evidence

ORD record
ord-701b623fbe76460383bad9b3cc235383
Source dataset
uspto-grants-2004_03
Patent number
US06703082B1

Reaction notes

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