Sodium Hydroxide → HCID 12040608, compound

HRID 1258538Notes

Reaction equation

HRID 1258538 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[C:9]([CH3:10])=[CH:8][C:7]([C:11]([F:20])([C:16]([F:19])([F:18])[F:17])[C:12]([F:15])([F:14])[F:13])=[CH:6][C:5]=1[CH3:21].[OH-].[Na+]>O1CCOCC1.CO>[CH3:21][C:5]1[CH:6]=[C:7]([C:11]([F:20])([C:12]([F:13])([F:14])[F:15])[C:16]([F:19])([F:18])[F:17])[CH:8]=[C:9]([CH3:10])[C:4]=1[C:3]([OH:22])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12040600HCID 12040600, compound

Product 1

HCID 12040608HCID 12040608, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

2,6-Dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-benzoic acid methyl ester (7 g, 0.021 mol) (Example I2) was dissolved in dioxane (70 ml) and methanol (15 ml), then aqueous sodium hydroxide (4N) (52.2 ml, 0.21 mol) was added. The mixture was stirred at 60° C. for 15 hours. The methanol was evaporated and the mixture was cooled to 0° C. before acidifying to pH=1 by addition of concentrated hydrochloric acid. The mixture was extracted three times with ethyl acetate. The combined organic phases were washed with water, dried over sodium sulfate and concentrated to give the 2,6-dimethyl-4-(1,2,2,2-tetra-fluoro-1-trifluoromethyl-ethyl)-benzoic acid (6.52 g, 98% yield). 1H-NMR (CDCl3, 400 MHz): 7.31 (s, 2H), 2.49 (s, 6H) ppm.

Workup

  1. customThe methanol was evaporated
  2. temperaturethe mixture was cooled to 0° C.
  3. additionbefore acidifying to pH=1 by addition of concentrated hydrochloric acid
  4. extractionThe mixture was extracted three times with ethyl acetate
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fbe335245f324a2e9313c8a2a3c558f6
Source dataset
uspto-grants-2013_06
Patent number
US08466180B2

Reaction notes

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