Benzene → 3-[4-(Trifluoromethyl)phenyl]-2-propynal

HRID 381445Notes

Reaction equation

HRID 381445 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][CH2:11][OH:12])=[CH:5][CH:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C1C=CC=CC=1>C(Cl)Cl>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:4]=[CH:5][C:6]([C:9]#[C:10][CH:11]=[O:12])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 159087TriacetoxyperiodinaneHCID 118304283-(4-(Trifluoromethyl)phenyl)prop-2-yn-1-ol

Product 1

HCID 183633083-[4-(Trifluoromethyl)phenyl]-2-propynalYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 20 ml of methylene chloride were dissolved 2.21 g (11.0 mmol) of 3-[4-(trifluoromethyl)phenyl]-2-propyn-1-ol, and 7.43 g (17.5 mmol) of Dess-Martin reagent were added to the solution under ice-cooling for 1.7 hours. Benzene was added to the resulting mixture and the insolubles were removed by filtration, followed by concentration of the filtrate to obtain 1.83 g (yield: 84%) of the title compound as an oil.

Workup

  1. additionwere added to the solution under ice-
  2. temperaturecooling for 1.7 hours
  3. customthe insolubles were removed by filtration

Sources & evidence

ORD record
ord-f62bd9873b784634b33abc45487c57d9
Source dataset
uspto-grants-2001_10
Patent number
US06306880B1

Reaction notes

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