Sulfuric Acid → Neopentyl 4-(trifluoromethyl)benzoate

HRID 1595986Notes

Reaction equation

HRID 1595986 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/hexanes25/75); IR 2932, 1727, 1327, 1280, 1133, 1066, 862, 775, 704 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.16 (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)δ 6 26.51, 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-f5ce0944dff44ed2ab45bfe1213a8586
Source dataset
uspto-grants-2001_09
Patent number
US06288242B1

Reaction notes

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