Thionyl Chloride → Benzoyl chloride, 4-(2,2-dimethyl-1-oxopropyl)-

HRID 1109311Notes

Reaction equation

HRID 1109311 reaction equation
[CH3:1][C:2]([CH3:15])([CH3:14])[C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][CH:6]=1)=[O:4].S(Cl)([Cl:18])=O>CN(C)C=O>[CH3:1][C:2]([CH3:15])([CH3:14])[C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([Cl:18])=[O:10])=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 119589814-(2,2-Dimethyl-1-oxopropyl)benzoic acid

Product 1

HCID 11806342Benzoyl chloride, 4-(2,2-dimethyl-1-oxopropyl)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 150.0 g (0.725 mol) of 4-(2,2-dimethyl-1-oxopropyl)-benzoic acid and 0.3 ml of dimethylformamide are added with stirring at 22° C. to 30° C. to 180 ml (2.47 mol) of thionyl chloride over a period of 60 minutes. The resulting solution is heated to an internal temperature of 85° to 90° C., and maintained at this temperature for 15 minutes. The solution is allowed to cool to 50° C. to remove as much thionyl chloride as possible by vacuum distillation (20-30 torr) at an internal temperature of 45° to 55° C. Distillation is discontinued when the internal temperature reaches 55° C and 95 ml of dry toluene are added. The distillation is continued under vacuum at an internal temperature of 45° to 55° C. and again discontinued when the internal temperature reaches 55° C. at 20-30 torr. After allowing the residue to cool to 25° C. and diluting it with 950 ml of dry toluene, the solution is set aside for use below.

Workup

  1. additionare added
  2. temperatureThe resulting solution is heated to an internal temperature of 85° to 90° C.
  3. temperaturemaintained at this temperature for 15 minutes
  4. customto remove as much thionyl chloride as
  5. distillationpossible by vacuum distillation (20-30 torr) at an internal temperature of 45° to 55° C
  6. distillationDistillation
  7. customreaches 55° C
  8. addition95 ml of dry toluene are added
  9. distillationThe distillation
  10. customis continued under vacuum at an internal temperature of 45° to 55° C.
  11. customreaches 55° C. at 20-30 torr
  12. temperatureto cool to 25° C.
  13. additiondiluting it with 950 ml of dry toluene

Sources & evidence

ORD record
ord-c84362601a2c4e4d954bb19f13674604
Source dataset
uspto-grants-1994_06
Patent number
US05319123

Reaction notes

Loading…