Thionyl Chloride → HCID 20371313, compound

HRID 616060Notes

Reaction equation

HRID 616060 reaction equation
[CH3:1][Si:2]([O:5][C:6](=[O:17])[CH:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8](O)=[O:9])([CH3:4])[CH3:3].CC(N([SiH3])[SiH3])=O.S(Cl)([Cl:26])=O>ClC1C=CC=CC=1>[Cl:26][C:8]([CH:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([O:5][Si:2]([CH3:4])([CH3:3])[CH3:1])=[O:17])=[O:9]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 13252699HCID 13252699, compoundHCID 71358606N,N-Disilylacetamide

Product 1

HCID 20371313HCID 20371313, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To a solution of phenylmalonic trimethylsilyl ester prepared with 0.1 mole of the acid (18.0) and bisilylacetamide in chlorobenzene (100 ml), there is added thionyl chloride (10 ml) with stirring being maintained at room temperature (20°) for 60 minutes. Thereafter the mixture is distilled at ordinary pressure to draw off trimethylchlorosilane (13.0 ml) and the resulting solution gives trimethylsilyl alpha-chlorocarbonyl-phenylacetate. Thereafter phenol (15.0 g) is added and stirring is continued at 45° C for 8 hours. The mixture is then washed with water and the pH is adjusted to 7.0 with sodium bicarbonate solution. The water phase is decanted off and the pH is adjusted to 5.0 with hydrochloric acid. The phenylmalonic acid phenyl monoester precipitates out, yield 95%, m.p. 105°-110°(d) and when recrystallised from benzene-n-hexane, has m.p. 116°-118° (d).

Workup

  1. distillationThereafter the mixture is distilled at ordinary pressure

Sources & evidence

ORD record
ord-9823b3ef68e74c5d9c569eac8be05d0d
Source dataset
uspto-grants-1978_02
Patent number
US04072710

Reaction notes

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