Acetovanillone → 4-(3-Chloropropoxy)-3-methoxyacetophenone

HRID 1902833Notes

Reaction equation

HRID 1902833 reaction equation
[CH3:1][C:2]([C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1)=[O:3].C([O-])([O-])=O.[K+].[K+].Br[CH2:20][CH2:21][CH2:22][Cl:23]>CC(C)=O>[C:2]([C:4]1[CH:12]=[CH:11][C:9]([O:10][CH2:20][CH2:21][CH2:22][Cl:23])=[C:6]([O:7][CH3:8])[CH:5]=1)(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 2214AcetovanilloneHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 88.0 g (0.53 mole) of acetovanillone in 375 ml of acetone was added 69.1 g (0.5 mole) of K2CO3. The mixture was allowed to reflux for 30 min. A solution of 110.2 g (0.70 mole) of 1-bromo-3-chloropropane in 75 ml of acetone was added dropwise. The mixture was heated at reflux for 20 h. The mixture was filtered and the filtrate concentrated under vacuum. The residual oil was distilled. An oil which weighed 110 g was obtained at 141°-143° C.0.1 mm Hg. The oil crystallised upon standing.

Workup

  1. temperatureto reflux for 30 min
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 20 h
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate concentrated under vacuum
  6. distillationThe residual oil was distilled
  7. customwas obtained at 141°-143° C
  8. customThe oil crystallised

Sources & evidence

ORD record
ord-119260e80e644a40aeb23397069754fa
Source dataset
uspto-grants-1982_12
Patent number
US04366162

Reaction notes

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