Sulfuric Acid → Neopentyl 4-(trifluoromethyl)benzoate

HRID 277453Notes

Reaction equation

HRID 277453 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[CH3:14][C:15]([CH3:19])([CH3:18])[CH2:16]O.S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH2:14][C:15]([CH3:19])([CH3:18])[CH3:16])=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6404Neopentyl alcoholHCID 99664-(Trifluoromethyl)benzoic acidHCID 10340Sodium Carbonate

Product 1

HCID 599219Neopentyl 4-(trifluoromethyl)benzoateYield 99.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 4-trifluoromethylbenzoic acid (75.0 g, 394 mmol) and 2,2-dimethyl-propyl alcohol (70.5 g, 800 mmol) in toluene (500 mL) was added concentrated sulfuric acid (3.0 mL). The mixture was stirred at reflux for 4 hours, cooled to room temperature, poured into saturated aqueous sodium carbonate (250 mL) and the layers were separated. The organic layer was washed with saturated aqueous sodium carbonate (250 mL), and brine (100 mL), and was concentrated to give 4-trifluoromethyl-benzoic acid, 2,2-dimethyl-propyl ester (102 g, 99% yield) as a yellow liquid: Rf: 0.66 (ethyl acetate/hexanes 25/75); IR 2932, 1727, 1327, 1280, 1133, 1066, 862, 775, 704 cm−1; 1H NMR (400 MHz, CDCl3) δ8.16 (d, J=7.9 Hz, 2H), 7.70 (d, J=8.1 Hz, 2H), 4.04 (s, 2H), 1.04 (s, 9); 13C NMR (100 MHz, CDCl3) δ26.51, 31.61, 74.72, 123.63 (q, J=272.7 HZ), 125.4, 129.9, 133.7, 134.35 (q, J=31.7 Hz), 165.35.

Workup

  1. temperatureat reflux for 4 hours
  2. customthe layers were separated
  3. washThe organic layer was washed with saturated aqueous sodium carbonate (250 mL), and brine (100 mL)
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-c7a1b840f5364511b62f39234356208e
Source dataset
uspto-grants-2002_03
Patent number
US06355825B1

Reaction notes

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