4'-Hydroxypropiophenone → 1-Propanone, 1-(4-(2-propenyloxy)phenyl)- (9CI)

HRID 1244149Notes

Reaction equation

HRID 1244149 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[CH:19]=[CH2:20]>CN(C=O)C>[CH2:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:6][CH:7]=1)[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 62714'-HydroxypropiophenoneHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 2004531-Propanone, 1-(4-(2-propenyloxy)phenyl)- (9CI)Yield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1-(4-hydroxy-phenyl)-propan-1-one (4.6 g, 30 mmol) and K2CO3 (5 g, 36 mmol) in DMF (10 mL) was added allylbromide (7.26 g, 60 mmol) dropwise with violent stirring. The reaction mixture was stirred at room temperature for 12 h and filtered to remove salt. The filtrate was concentrated to yield the titled compound (5.5 g, 97%) as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ 7.94 (d, 2H, J=9.0 Hz), 7.05 (d, 2H, J=9.0 Hz), 6.05 (m, 1H), 5.44, 5.38, 5.30, 5.26 (4d, 2H, J=3.0 Hz), 4.66 (d, 2H, J=6.0 Hz), 2.98 (q, 2H, J=7.5 Hz), 1.07 (t, 3H, J=7.5 Hz). MS (ESI) m/e 191 (M+H)+; 189 (M−H)−.

Workup

  1. filtrationfiltered
  2. customto remove salt
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-edd0178b38a84c5c9d989b36195e894a
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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