Hydrochloric Acid → 3,3-Dichloro-2-(4-trifluoromethyl-phenyl)-acrylic acid

HRID 1869138Notes

Reaction equation

HRID 1869138 reaction equation
C([O:3][C:4](=[O:19])[C:5]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)=[C:6]([Cl:8])[Cl:7])C.O1CCCC1.[OH-].[Li+].Cl>O>[Cl:7][C:6]([Cl:8])=[C:5]([C:9]1[CH:10]=[CH:11][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:13][CH:14]=1)[C:4]([OH:19])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 866130793,3-Dichloro-2-(4-trifluoromethyl-phenyl)-acrylic acid ethyl ester

Product 1

HCID 866130803,3-Dichloro-2-(4-trifluoromethyl-phenyl)-acrylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

P1.2): 650 mg of 3,3-dichloro-2-(4-trifluoromethyl-phenyl)-acrylic acid ethyl ester are introduced into 4 ml of tetrahydrofuran. 100 mg of lithium hydroxide in 1.5 ml of water are then added and the mixture is stirred at room temperature for 16 hours. After a further 4 hours at 40° C., the reaction mixture is poured into water, rendered acidic with concentrated hydrochloric acid and extracted with ethyl acetate. The organic phases are washed twice with water and concentrated. 3,3-Dichloro-2-(4-trifluoromethyl-phenyl)-acrylic acid is obtained.

Workup

  1. waitAfter a further 4 hours at 40° C.
  2. extractionextracted with ethyl acetate
  3. washThe organic phases are washed twice with water
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-85f644298f2a406681db5cc709b300ad
Source dataset
uspto-grants-2009_12
Patent number
US07638514B2

Reaction notes

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