Acetovanillone → 1-(4-Benzyloxy-3-methoxy-phenyl)-ethanone

HRID 1754240Notes

Reaction equation

HRID 1754240 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[O:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>[I-].[K+].CC(C)=O>[CH2:19]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[O:11][CH3:12])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 2214AcetovanilloneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 992151-(4-Benzyloxy-3-methoxy-phenyl)-ethanoneYield 98%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

The mixture of 31.62 g (190 mmol) 1-(4-hydroxy-3-methoxy-phenyl)-ethanone, 16.36 g (118 mmol) potassium carbonate, 0.5 g potassium iodide, 400 ml acetone and 33.15 g (190 mmol) ml benzyl bromide were refluxed for 2 days. The solvent was evaporated, the residue was taken up in 400 ml of water. The precipitate was filtered, washed with 100 ml of sodium carbonate saturated aqueous solution and 2×100 ml of water, then dried on air to give 47.8 g of product [A]. Yield 98%.

Workup

  1. temperaturewere refluxed for 2 days
  2. customThe solvent was evaporated
  3. filtrationThe precipitate was filtered
  4. washwashed with 100 ml of sodium carbonate saturated aqueous solution and 2×100 ml of water
  5. customdried on air

Sources & evidence

ORD record
ord-f35106a44c1d41bea7646473f54bdc6d
Source dataset
uspto-grants-2015_10
Patent number
US09169241B2

Reaction notes

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