p-Toluenesulfonic acid monohydrate → 1,2-Dimethyl-3-(prop-2-en-1-yl)benzene

HRID 2167229Notes

Reaction equation

HRID 2167229 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](O)([CH3:11])C.O.[C:14]1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:9][CH:11]=[CH2:14])[C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 235905312-(2,3-Dimethylphenyl)propan-2-ol

Product 1

HCID 206267321,2-Dimethyl-3-(prop-2-en-1-yl)benzeneYield 92%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-(2,3-Dimethylphenyl)propan-2-ol, compound of formula (XXIV), prepared according to either example 1 or example 2, (1.10 g, 6.70 mmol), was dissolved in benzene (20 mL), and p-toluenesulfonic acid monohydrate (35 mg, 0.18 mmol) was added. The mixture was stirred at room temperature for 3 h. Silica gel (200 mg) was added, and stirring was continued for ca. 16 hours, and then the reaction mixture was refluxed for 30 min. After cooling to room temperature, the mixture was filtered, washed with aqueous K2CO3 solution, conventionally dried, and concentrated under reduced pressure, to yield 0.90 g (92%) of the title compound. 1H NMR: 2.02 (m, 3H), 2.21 (s, 3H), 2.28 (s, 3H), 4.82 (m, 1H), 5.17 (m, 1H), 6.97 (m, 1H), 7.05 (m, 2H).

Workup

  1. additionSilica gel (200 mg) was added
  2. stirringstirring
  3. waitwas continued for ca. 16 hours
  4. temperaturethe reaction mixture was refluxed for 30 min
  5. temperatureAfter cooling to room temperature
  6. filtrationthe mixture was filtered
  7. washwashed with aqueous K2CO3 solution
  8. customconventionally dried
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6931f278ead442209dfc8f3895cd7735
Source dataset
uspto-grants-2015_06
Patent number
US09045433B2

Reaction notes

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