Water → 4-Tert-butyl-2-methylbenzoic acid

HRID 2236440Notes

Reaction equation

HRID 2236440 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH3:12])[C:8]([CH3:11])=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[OH2:13].[Mn]([O-])(=O)(=O)=[O:15].[K+]>N1C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([OH:15])=[O:13])=[C:7]([CH3:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 81881Benzene, 4-(1,1-dimethylethyl)-1,2-dimethyl-HCID 516875Potassium Permanganate

Product 1

HCID 119589774-Tert-butyl-2-methylbenzoic acidYield 8.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

An amount of 10.0 g (61.62 mmol) of 4-tert-butyl-o-xylene is added to 100 mL solution of 20% water in pyridine and stirred at 80° C. for one hour. 25 g (154.05 mmol) of potassium permanganate is also added and continued to stir at 80° C. for three hours more. After cooling to room temperature, the mixture is filtered through a thick pack of celite and washed many times with water. The water layer is acidify to pH ˜2, and the precipitate is filtered and crystallized out of water: methanol to give 2.4 g (8.5% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6) □ 1.282 (S, 9H), 2.530 (S, 3H), 7.295 (d, J=6.9 Hz 2H), 7.821 (d, J=2.1 Hz 1H). Ref: JACS, 66, 154-5(1944)

Workup

  1. stirringto stir at 80° C. for three hours more
  2. temperatureAfter cooling to room temperature
  3. filtrationthe mixture is filtered through a thick pack of celite
  4. washwashed many times with water
  5. filtrationthe precipitate is filtered
  6. customcrystallized out of water
  7. custommethanol to give 2.4 g (8.5% yield) as a white solid

Sources & evidence

ORD record
ord-af835b2714bf4cb7bc2af2445fc92904
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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