Carbon Dioxide → Trimethylsilyl trichloroacetate

HRID 2198999Notes

Reaction equation

HRID 2198999 reaction equation
C1(O)C=CC=CC=1.[Cl:8][C:9]([Cl:18])([Cl:17])[C:10]([O:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C(=O)([O-])[O-].[K+].[K+].C(=O)=O>C(Cl)(Cl)Cl>[C:9]([Si:13]([CH3:14])([CH3:15])[CH3:16])([Cl:18])([Cl:17])[Cl:8].[Cl:18][C:9]([Cl:8])([Cl:17])[C:10]([O:12][Si:13]([CH3:14])([CH3:15])[CH3:16])=[O:11]

Participants

7

Reactant 4

HCID 280Carbon Dioxide2×HCID 996PhenolHCID 11430Potassium CarbonateHCID 117484Trimethylsilyl trichloroacetate

Product 2

HCID 117484Trimethylsilyl trichloroacetateHCID 3372381trimethyl(trichloromethyl)silane

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
150 °C

Procedure

Phenol (1.17 g, 0.0125 mole), trimethylsilyl trichloroacetate (3.53 g, 0.015 mole), potassium carbonate (0.035 g) and 18-crown-6 polyether (0.066 g) were placed in a 25-ml round-bottom flask fitted with a distillation head. A dry ice receiver and dry ice trap were attached. The mixture was heated to 150° C. Gas evolution proceeded rapidly and liquid chloroform and CCl3SiMe3 (formed by the base-induced decomposition of trimethylsilyl trichloroacetate) collected in the dry ice trap.

Workup

  1. customfitted with a distillation head

Sources & evidence

ORD record
ord-bcc5525e9a8f46a7b8814a656756e7d5
Source dataset
uspto-grants-1982_11
Patent number
US04360686

Reaction notes

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