Trichloroacetic Acid → 2,2,2-Trichloro-1,1-di(2,3,4,5,6-pentafluorophenyl)-1-ethanol

HRID 428352

Reaction equation

HRID 428352 reaction equation
[F:1][C:2]1[C:7]([C:8](=[O:20])[C:9]2[C:14]([F:15])=[C:13]([F:16])[C:12]([F:17])=[C:11]([F:18])[C:10]=2[F:19])=[C:6]([F:21])[C:5]([F:22])=[C:4]([F:23])[C:3]=1[F:24].[Cl:25][C:26]([Cl:31])([Cl:30])C(O)=O.FF.C([O-])(=O)C=C>CO.CN(C)P(N(C)C)(N(C)C)=O>[Cl:25][C:26]([Cl:31])([Cl:30])[C:8]([C:9]1[C:10]([F:19])=[C:11]([F:18])[C:12]([F:17])=[C:13]([F:16])[C:14]=1[F:15])([C:7]1[C:2]([F:1])=[C:3]([F:24])[C:4]([F:23])=[C:5]([F:22])[C:6]=1[F:21])[OH:20]

Participants

7

Reactant 4

HCID 6421Trichloroacetic AcidHCID 24524FluorineHCID 25188AcrylateHCID 70068Decafluorobenzophenone

Product 1

HCID 226252562,2,2-Trichloro-1,1-di(2,3,4,5,6-pentafluorophenyl)-1-ethanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4.9 g of decafluorobenzophenone and 2.7 g of trichloroacetic acid was added to 15 mL of hexamethylphosphoramide. The stirred reaction mixture was maintained at about 0° C. for about 2 hours and then allowed to warm to room temperature and continue stirring at ambient temperature for the next 15 hours. The reaction mixture was characterized by GC and fluorine NMR to show a conversion of approximately 20% to the desired carbinol. This carbinol can be converted to the corresponding acrylate by methods previously described (cf. Example 24).

Workup

  1. customThe stirred reaction mixture
  2. temperatureto warm to room temperature

Sources & evidence

ORD record
ord-9797598e0f8945dcacc0fb81a52e30ac
Source dataset
uspto-grants-2001_11
Patent number
US06313245B1

Linked notes

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