Hydrochloric Acid → Methyl 3-hydroxy-2-(alpha,alpha,alpha-trifluoro-m-tolyl)acrylate

HRID 1087570Notes

Reaction equation

HRID 1087570 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH:16](OC)=[O:17].[Na].Cl>C(OCC)C>[OH:17][CH:16]=[C:9]([C:5]1[CH:4]=[C:3]([C:2]([F:14])([F:15])[F:1])[CH:8]=[CH:7][CH:6]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7865Methyl formateHCID 2734603Methyl (3-(trifluoromethyl)phenyl)acetateHCID 5360545Sodium

Product 1

HCID 67828062Methyl 3-hydroxy-2-(alpha,alpha,alpha-trifluoro-m-tolyl)acrylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

aa) 26.2 g of methyl 3-trifluoromethylphenylacetate were dissolved in 100 ml of diethyl ether and after the addition of 8.2 ml of methyl formate, treated with 2.76 g of sodium. The mixture was stirred at room temperature until the reaction was completed and treated with 1N hydrochloric acid while cooling. The organic phase was separated and the aqueous phase was extracted twice with ether. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated. Distillation yielded methyl 3-hydroxy-2-(α,α,α-trifluoro-m-tolyl)acrylate as a colorless oil of b.p. 59°-62°/0.2 mm.

Workup

  1. temperaturewhile cooling
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted twice with ether
  4. washThe combined organic phases were washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. distillationDistillation

Sources & evidence

ORD record
ord-9d9e00d9c65f44e4a420bc8a683b0c17
Source dataset
uspto-grants-1991_07
Patent number
US05036066

Reaction notes

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