Water → 3-(4-Trifluoromethylphenylthio)propanal

HRID 703291Notes

Reaction equation

HRID 703291 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.[CH:12]([CH:14]=[CH2:15])=[O:13].O>C1COCC1.C(N(CC)CC)C>[F:11][C:2]([F:1])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([S:9][CH2:15][CH2:14][CH:12]=[O:13])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7847AcroleinHCID 1366534-(Trifluoromethyl)thiophenol

Product 1

HCID 143479823-(4-Trifluoromethylphenylthio)propanalYield 99.6%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ten grams of 4-trifluoromethylthiophenol was dissolved in 15 ml of THF, and after adding 4.0 g of 95% acrolein under ice-cooling, 0.1 g of triethylamine was added while thoroughly stirring the reaction solution. After stirring for 1.5 hours under ice-cooling, the reaction solution was poured into water and extracted with ether. The ether layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 13.1 g of 3-(4-trifluoromethylphenylthio)propionaldehyde.

Workup

  1. temperaturecooling
  2. stirringAfter stirring for 1.5 hours under ice-
  3. temperaturecooling
  4. extractionextracted with ether
  5. washThe ether layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d48828d6e68a4285a918474b1146e3e3
Source dataset
uspto-grants-1991_01
Patent number
US04981971

Reaction notes

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