Methyl vinyl ketone → 4-[(4-Methoxyphenyl)methoxy]butan-2-one

HRID 1701858Notes

Reaction equation

HRID 1701858 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[CH:11]([C:13]([CH3:15])=[O:14])=[CH2:12]>S(=O)(=O)(O)O.C(OCC)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][O:8][CH2:12][CH2:11][C:13](=[O:14])[CH3:15])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 77384-Methoxybenzyl alcohol

Product 1

HCID 131169094-[(4-Methoxyphenyl)methoxy]butan-2-one

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

Combine 4-methoxybenzyl alcohol (13.8 g, 0.10 mole) with methyl vinyl ketone (8.4 g, 0.12 mole), treat with 5 drops of concentrated sulfuric acid, and stir 1 hour. Dilute with ethyl ether, wash with 1.0 N sodium bicarbonate solution, dry the organic phase over anhydrous sodium sulfate and evaporate in vacuo to obtain the title compound, m.p. 48-9° C.

Workup

  1. washwash with 1.0 N sodium bicarbonate solution
  2. dry with materialdry the organic phase over anhydrous sodium sulfate
  3. customevaporate in vacuo

Sources & evidence

ORD record
ord-79a8b21d572642f5b572efbccc069c68
Source dataset
uspto-grants-1983_04
Patent number
US04379166

Reaction notes

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