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

HRID 1702537Notes

Reaction equation

HRID 1702537 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>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=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

6

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 69.7%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-(4-chlorophenyl)benzaldehyde (15.0 g.), 2-hydroxy-2-methylpropionic acid (10.0 g.) and p-toluenesulphonic acid monohydrate (0.2 g.) was heated in toluene (200 ml.) under reflux for 6 hours with continuous removal of water by azeotropic distillation. The solution was then cooled, washed with 10% w/v sodium hydrogen carbonate solution (100 ml.) and then with water (2×100 ml.) before it was dried (Na2SO4). The dried toluene solution was filtered and evaporated to give 2-[4-(4-chlorophenyl)phenyl]-5,5-dimethyl-1,3-dioxolan-4-one (14.6 g.), m.p. 108°-110° C. (after recrystallisation from cyclohexane and then from toluene).

Workup

  1. temperatureThe solution was then cooled
  2. washwashed with 10% w/v sodium hydrogen carbonate solution (100 ml.)
  3. dry with materialwith water (2×100 ml.) before it was dried (Na2SO4)
  4. filtrationThe dried toluene solution was filtered
  5. customevaporated

Sources & evidence

ORD record
ord-c48283afc8bb4ef6bf62b3a56c0cb84a
Source dataset
uspto-grants-1982_09
Patent number
US04348322

Reaction notes

Loading…