Guaiacol → 1-(4-Hydroxy-3-methoxyphenyl)butan-1-one

HRID 274447Notes

Reaction equation

HRID 274447 reaction equation
[C:1]1([O:8][CH3:9])[C:2](=[CH:4][CH:5]=[CH:6][CH:7]=1)[OH:3]>C(OC(=O)CCC)(=O)CCC.[Cl-].[Zn+2].[Cl-]>[OH:3][C:2]1[CH:4]=[CH:5][C:6]([C:2](=[O:3])[CH2:1][CH2:7][CH3:6])=[CH:7][C:1]=1[O:8][CH3:9]

Participants

4

Reactant 1

HCID 460Guaiacol

Product 1

HCID 140350981-(4-Hydroxy-3-methoxyphenyl)butan-1-one

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 7798Butyric anhydrideSolvent

Procedure

100 g of guaiacol are dissolved in 136.4 g of butyric anhydride, treated with 120 g of zinc chloride, heated for 3 minutes as given in Example 6.a and then worked-up as described there. The crude product obtained after high vacuum distillation is chromatographed with toluene on 600 g of silica gel. After recrystallization from ether/n-hexane there is obtained 4'-hydroxy-3'-methoxy-butyrophenone in the form of colorless crystals of m.p. 40°-41°.

Workup

  1. temperatureheated for 3 minutes
  2. customThe crude product obtained
  3. distillationafter high vacuum distillation
  4. customis chromatographed with toluene on 600 g of silica gel
  5. customAfter recrystallization from ether/n-hexane there

Sources & evidence

ORD record
ord-ecc99229464a4e68bac35c19ae6f9a00
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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