Water → 4-(Chloromethyl)-2-[(4-chlorophenyl)methyl]-2-phenyl-1,3-dioxolane

HRID 979538Notes

Reaction equation

HRID 979538 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.[Cl:17][CH2:18][CH:19](O)[CH2:20][OH:21].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Cl:17][CH2:18][CH:19]1[CH2:20][O:21][C:9]([CH2:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[O:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 72903-Chloro-1,2-propanediolHCID 95829Ethanone, 2-(4-chlorophenyl)-1-phenyl-

Product 1

HCID 132642114-(Chloromethyl)-2-[(4-chlorophenyl)methyl]-2-phenyl-1,3-dioxolaneYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

69 g (0.3 mol) of phenyl 4-chlorophenylmethyl ketone, 66.3 g (0.6 mol) of 3-chloropropane-1,2-diol and 5.2 g (0.03 mol) of p-toluenesulphonic acid in 600 ml of toluene are refluxed for three days in a water separator. The reaction mixture, when it is cold, is extracted with sodium bicarbonate solution, dried over sodium sulphate and evaporated down in vacuo. 95 g (98% of theory) of 4-chloromethyl-2-(4-chlorophenylmethyl)-2-phenyl-1,3-dioxolane of melting point 65° C. are obtained.

Workup

  1. extractionis extracted with sodium bicarbonate solution
  2. dry with materialdried over sodium sulphate
  3. customevaporated down in vacuo

Sources & evidence

ORD record
ord-44a64784046645b79dd207cb255a6265
Source dataset
uspto-grants-1987_05
Patent number
US04668700

Reaction notes

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