Water → 2-[4-(4-Chlorophenyl)phenyl]-5,5-dimethyl-1,3-dioxolan-4-one

HRID 1702543Notes

Reaction equation

HRID 1702543 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.O[C:17]([CH3:22])([CH3:21])[C:18]([OH:20])=[O:19].O>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]3[O:20][C:18](=[O:19])[C:17]([CH3:22])([CH3:21])[O:13]3)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 116712-Hydroxyisobutyric acidHCID 5925704'-Chloro[1,1'-biphenyl]-4-carbaldehyde

Product 1

HCID 127737612-[4-(4-Chlorophenyl)phenyl]-5,5-dimethyl-1,3-dioxolan-4-oneYield 39.8%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 4-(4-chlorophenyl)benzaldehyde (21.6 g.), 2-hydroxy-2-methylpropionic acid (10.2 g.) and cationic sulphonated polystyrene ion exchange resin (`AMBERLITE` *IR 120, free acid form; 2.0 g.) in chlorobenzene (125 ml.) was heated under reflux for 24 hours with continuous removal of water by azeotropic distillation. The mixture was cooled and the resin was separated by filtration. Pyridine (3 ml.) was added to the filtrate which was then evaporated. The residue was dissolved in hot 2-propanol (200 ml.). A small quantity of insoluble material was removed by filtration and the subsequent filtrate was allowed to cool to give 2-[4-(4-chlorophenyl)phenyl]-5,5-dimethyl-1,3-dioxolan-4-one (11.8 g.), m.p. 108°-110° C.

Workup

  1. temperatureThe mixture was cooled
  2. customthe resin was separated by filtration
  3. additionPyridine (3 ml.) was added to the filtrate which
  4. customwas then evaporated
  5. dissolutionThe residue was dissolved in hot 2-propanol (200 ml.)
  6. customA small quantity of insoluble material was removed by filtration
  7. temperatureto cool

Sources & evidence

ORD record
ord-6bd19959861b45a6b018456baddcfff1
Source dataset
uspto-grants-1982_09
Patent number
US04348322

Reaction notes

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