Dimethylformamide → 1-[2-Hydroxy-4-(phenylmethoxy)-3-(3-phenylpropyl)phenyl]ethanone

HRID 2210078Notes

Reaction equation

HRID 2210078 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:6]([OH:17])[CH:5]=[CH:4][C:3]=1[C:18](=[O:20])[CH3:19].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CC(C)=O>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[C:6]([O:17][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:5]=[CH:4][C:3]=1[C:18](=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 193799221-[2,4-Dihydroxy-3-(3-phenylpropyl)phenyl]ethanone

Product 1

HCID 193799211-[2-Hydroxy-4-(phenylmethoxy)-3-(3-phenylpropyl)phenyl]ethanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6.69 g (24.7 mmol) of 1-[2,4-dihydroxy-3-(3-phenylpropyl)phenyl]ethanone, from the preceding example, 5.35 g (31.3 mmol) of benzyl bromide, 14.9 g (0.108 mol)of anhydrous potassium carbonate, 115 mL of dry N,N-dimethylformamide, and 230 mL of acetone was stirred and refluxed for 8 hr. After being cooled, the slurry was filtered with suction and the solids washed well with acetone. The filtrate and washes were combined and concentrated under reduced pressure to give a yellow oil which was chromatographed on silica gel. There was obtained 5.57 g (62.6%) of the desired monoether as a pale-yellow solid. Recrystallization of a sample from hexane-ethyl acetate gave the title compound as colorless needles, mp 115°-116° C.

Workup

  1. temperaturerefluxed for 8 hr
  2. temperatureAfter being cooled
  3. filtrationthe slurry was filtered with suction
  4. washthe solids washed well with acetone
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow oil which
  7. customwas chromatographed on silica gel
  8. customThere was obtained 5.57 g (62.6%) of the desired monoether as a pale-yellow solid
  9. customRecrystallization of a sample from hexane-ethyl acetate

Sources & evidence

ORD record
ord-d2546e8679ca4776834c19c028dfdd67
Source dataset
uspto-grants-1995_10
Patent number
US05457124

Reaction notes

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