(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acid → Benzeneacetic acid, 4-(trifluoroMethyl)-, Methyl ester

HRID 1475632Notes

Reaction equation

HRID 1475632 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[CH3:15][Si](C=[N+]=[N-])(C)C>C1(C)C=CC=CC=1.CO.C(OCC)C>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH3:15])=[O:11])=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 12717573Benzeneacetic acid, 4-(trifluoroMethyl)-, Methyl ester

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

6.0 g (29.4 mmol) of [4-(trifluoromethyl)phenyl]acetic acid were dissolved in 67.1 ml of toluene and 46.2 ml of methanol, and 26.5 ml (52.9 mmol) of a 2 M solution of trimethylsilyldiazomethane in diethyl ether were added dropwise with cooling. After the addition had ended, cooling was removed and the mixture was stirred at RT for another 1 h, after which excess trimethylsilyldiazomethane was destroyed by addition of 2.0 ml of acetic acid. The reaction mixture was concentrated under reduced pressure and the crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 80:1). This gave 4.33 g of the target compound (67.6% of theory).

Workup

  1. temperaturewith cooling
  2. additionAfter the addition
  3. temperaturecooling
  4. customwas removed
  5. customafter which excess trimethylsilyldiazomethane was destroyed by addition of 2.0 ml of acetic acid
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. customthe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 80:1)

Sources & evidence

ORD record
ord-b4b7b6379ce24be7898de4d912699fac
Source dataset
uspto-grants-2015_04
Patent number
US09018258B2

Reaction notes

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