Acetone → 7-(Benzyloxy)naphthalen-2-ol

HRID 217159Notes

Reaction equation

HRID 217159 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=CC=[CH:10][CH:9]=1.[CH3:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[C:21]([O:24][CH2:25][CH3:26])(=O)C.[CH3:27][C:28]([CH3:30])=[O:29]>>[CH2:21]([O:24][C:25]1[CH:26]=[CH:13][C:8]2[C:9](=[CH:27][C:28]([OH:29])=[CH:30][CH:7]=2)[CH:10]=1)[C:17]1[CH:16]=[CH:15][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexane

Product 1

HCID 27638187-(Benzyloxy)naphthalen-2-ol

Procedure

A stirred solution of 2,7-dihydroxynaphthylene (4.8 g) in acetone (50 ml) containing anhydrous potassium carbonate (4.08 g) and benzyl bromide (5.13 g0 was heated to refax for 4 hours, cooled to ambient temperature then stored for 18 hours. The mixture was filtered and the filtrate evaporated under reduced pressure to give a pale green solid that was fractionated by chromatography (silica; hexane/ethyl acetate 95:5 to 1:1 by volume) to give 2-benzyloxynaphth-7-ol, 1.63 g, as a cream coloured solid, m.p. 152-154° C.

Workup

  1. temperaturewas heated
  2. waitthen stored for 18 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated under reduced pressure
  5. customto give a pale green solid that

Sources & evidence

ORD record
ord-c64c32f391d0412ca2a9ef2e61e693e6
Source dataset
uspto-grants-2012_06
Patent number
US08193361B2

Reaction notes

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