Ethanol → 2-(3,4,4-Trifluoro-3-butenyl)malonic acid

HRID 6470Notes

Reaction equation

HRID 6470 reaction equation
[OH-].[K+].C(O)C.[F:6][C:7](=[C:31]([F:33])[F:32])[CH2:8][CH2:9][CH:10]([C:21]([O:23]CC1C=CC=CC=1)=[O:22])[C:11]([O:13]CC1C=CC=CC=1)=[O:12]>O>[F:6][C:7](=[C:31]([F:32])[F:33])[CH2:8][CH2:9][CH:10]([C:21]([OH:23])=[O:22])[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 19793830HCID 19793830, compound

Product 1

HCID 197938502-(3,4,4-Trifluoro-3-butenyl)malonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

5.56 g (99 mmol) KOH flakes were dissolved in 6.82 ml water and 13.65 ml ethanol and then treated with 11.12 g (28.34 mmol) of dibenzyl 2-(3,4,4-trifluoro-3-butenyl)-malonate. After heating under reflux for 4 hours, the reaction mixture was poured into 30 ml water and washed with ether. The aqueous phase was acidified with dilute hydrochloric acid and extracted 4 times with ether. The organic phase was dried over sodium sulphate, filtered and then concentrated in a rotary evaporator.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 4 hours
  3. washwashed with ether
  4. extractionextracted 4 times with ether
  5. dry with materialThe organic phase was dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record
ord-10fea42bec564443a9bc5ae1ea51daad
Source dataset
uspto-grants-1993_09
Patent number
US05248810

Reaction notes

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