Hydrochloric Acid → 2,2,2-Triphenylacetyl chloride

HRID 404531Notes

Reaction equation

HRID 404531 reaction equation
[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](O)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:26])=O.Cl>CN(C)C=O.ClCCl>[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([Cl:26])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 68992Triphenylacetic acid

Product 1

HCID 3472012,2,2-Triphenylacetyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of triphenylacetic acid (21.7 g; 0.075 mol) and dry dimethylformamide (2 drops) in dry dichloromethane (100 cm3) was treated with oxalyl chloride (14 g; 0.11 mol) which was added in 4 approximately equal portions over ˜25 minutes. The mixture was stirred at 35° until evolution of hydrogen chloride had ceased (˜4 hrs). The resulting colourless solution was evaporated in vacuo at 40° to constant weight to give the title compound as a colourless crystalline solid. Yield=23.24 g (100.0%). The product was used directly in next stage.

Workup

  1. additionwas added in 4 approximately equal portions over ˜25 minutes
  2. custom(˜4 hrs)
  3. customThe resulting colourless solution was evaporated in vacuo at 40° to constant weight

Sources & evidence

ORD record
ord-969c68b93b044867b1fc66c828732571
Source dataset
uspto-grants-2014_06
Patent number
US08748599B2

Reaction notes

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