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2-Propenoic acid, 3-[4-(trifluoromethyl)phenyl]-, ethyl ester → (E)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-ol

HRID 1601366
Notes
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Reaction equation

HRID 1601366 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:15]=[CH:14][C:6](/[CH:7]=[CH:8]/[C:9](OCC)=[O:10])=[CH:5][CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:15]=[CH:14][C:6](/[CH:7]=[CH:8]/[CH2:9][OH:10])=[CH:5][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 115070152-Propenoic acid, 3-[4-(trifluoromethyl)phenyl]-, ethyl esterHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 10512285(E)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-olYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

In 15 ml of toluene were dissolved 3.00 g (12.3 mmol) of ethyl trans-4-(trifluoromethyl)cinnamate, and 16.4 ml (24.6 mmol) of a 1.5M diisobutyl aluminum hydride-toluene solution were added to the solution with stirring at 0° C. After 20 minutes, ice-water was added to the reaction mixture and the mixture was stirred for 10 minutes, followed by removal of the insolubles by filtration using Celite. The filtrate was extracted with ethyl acetate and, after drying, the solvent was distilled off to obtain a crystalline residue. The residue was recrystallized from a mixed solvent of benzene-hexane to obtain 2.36 g (yield: 96%) of the title compound having a melting point of 53 to 55° C.

Workup

  1. additionwere added to the solution
  2. stirringthe mixture was stirred for 10 minutes
  3. customfollowed by removal of the insolubles by filtration
  4. extractionThe filtrate was extracted with ethyl acetate
  5. customafter drying
  6. distillationthe solvent was distilled off
  7. customto obtain a crystalline residue
  8. customThe residue was recrystallized from a mixed solvent of benzene-hexane

Sources & evidence

ORD record
ord-4a627d93cc344a16afab0ee5fa969d3b
Source dataset
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05977152

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes