Bromomethyl 4-methoxyphenyl ketone → HCID 19908834, compound

HRID 1535057Notes

Reaction equation

HRID 1535057 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[OH:18])=O.[CH3:19][O:20][C:21]1[CH:30]=[CH:29][C:24]([C:25](=O)[CH2:26]Br)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:19][O:20][C:21]1[CH:30]=[CH:29][C:24]([CH2:25][C:26]2[O:18][C:5]3[CH:6]=[CH:7][C:8]([O:10][CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[CH:9][C:4]=3[C:2]=2[CH3:1])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 11430Potassium CarbonateHCID 128709281-[5-(Benzyloxy)-2-hydroxyphenyl]ethan-1-one

Product 1

HCID 19908834HCID 19908834, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-hydroxy-5-benzyloxyacetophenone (93 g, 380 mmoles), p-methoxyphenacyl bromide (88 g, 384 mmoles) and potassium carbonate (106 g, 768 mmoles) in acetone (1.5 L) was refluxed for 46 hours. The reaction mixture was cooled and filtered. The filtrate was evaporated in vacuo. The residue was chromatographed on silica gel using 10% ethylacetate in hexane as eluent to yield (127 g, 89%) of 2-(p-methoxybenzyl)-3-methyl-5-benzyloxybenzofuran, E48.

Workup

  1. temperaturewas refluxed for 46 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated in vacuo
  5. customThe residue was chromatographed on silica gel using 10% ethylacetate in hexane as eluent

Sources & evidence

ORD record
ord-94ea4f246d0142e0a868d62d707e9ced
Source dataset
uspto-grants-1992_02
Patent number
US05091533

Reaction notes

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