Ethyl Acetate → 4-(2,2-Dimethylpropyl)benzoic acid

HRID 1268923Notes

Reaction equation

HRID 1268923 reaction equation
[CH3:1][C:2]([CH3:13])([CH3:12])[CH2:3][C:4]1(C=C)[CH:9]=[CH:8][CH:7]=[CH:6][CH2:5]1.CC[O:16][C:17](C)=[O:18]>O>[CH3:13][C:2]([CH3:1])([CH3:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:17]([OH:18])=[O:16])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 8857Ethyl Acetate2×HCID 866014194-(2,2-Dimethylpropyl)4-ethenylbenzene

Product 1

HCID 81670894-(2,2-Dimethylpropyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of 1.74 g (7.76 mmol) of 4-(2,2-dimethylpropyl)-4-ethenylbenzene (from Step A) in 10 mL EtOAc and 10 mL H2O was added 8.30 g (38.8 mmol) of NaIO4 and 1 mg (0.0078 mmol) RuO2. The reaction mixture was heated to 40° C. for 30 min. The reaction mixture was cooled and stirred at rt for 16 hr. To the reaction mixture was added H2O and EtOAc, and layers were separated. The organic layer was dried and concentrated to dryness to provide 776 mg of the title compound: 1H NMR (500 Mhz) δ 0.91 (s, 9H), 2.53 (s, 2H), 7.12 (d, J=8.0, 2H), 7.84 (d, J=8.0, 2H); ESI-MS 193 (M+H); LC-1: 3.2 min.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customwere separated
  3. customThe organic layer was dried
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-19f77993086d4b20bb5bbb231240b33e
Source dataset
uspto-grants-2007_04
Patent number
US07199142B2

Reaction notes

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