Water → HCID 22611734, compound

HRID 1902611Notes

Reaction equation

HRID 1902611 reaction equation
[C:1]1(OC)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].Cl[CH2:14][CH2:15][CH2:16][C:17]([Cl:19])=[O:18].[OH2:20]>ClC1C=CC=CC=1>[Cl:19][CH:17]([OH:18])[CH2:16][CH2:15][C:14]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 7519AnisoleHCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22611734HCID 22611734, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
100 °C

Procedure

32.4 g of anisole are dissolved in 30 ml of chlorobenzene. 53.6 g of AlCl3 are introduced in portions, at not more than 35° C., with ice-cooling. 42.3 g of γ-chlorobutyric acid chloride are added dropwise at a temperature of 15°-35° C. and the mixture is then slowly warmed to 100° C. After stirring for three hours at 100° C., the mixture is cooled to room temperature and discharged into water and the mixture is then extracted with ether. Evaporation of the ether phase, after this has been washed until neutral and dried, yields a reddish solid. This is recrystallised from hexane/ethanol using active charcoal. 45 g of γ-chloro-4-hydroxybutyrophenone of the formula: ##STR42## are then obtained in the form of colourless crystals with a melting point of 108°-111° C.

Workup

  1. temperaturecooling
  2. temperaturethe mixture is cooled to room temperature
  3. extractionthe mixture is then extracted with ether
  4. customEvaporation of the ether phase
  5. washafter this has been washed until neutral and
  6. customdried
  7. customyields a reddish solid
  8. customThis is recrystallised from hexane/ethanol using active charcoal

Sources & evidence

ORD record
ord-7d4a1fa8ba6e4440acc25316cc07b69e
Source dataset
uspto-grants-1982_12
Patent number
US04364949

Reaction notes

Loading…