p-Toluenesulfonic acid monohydrate → 1,3-Benzodioxole, 5-(1-methylethenyl)-

HRID 486938Notes

Reaction equation

HRID 486938 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](O)([CH3:12])[CH3:11])=[CH:9][C:4]=2[O:3][CH2:2]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([CH3:12])=[CH2:11])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 118196322-(Benzo[d][1,3]dioxol-5-yl)propan-2-ol

Product 1

HCID 112866271,3-Benzodioxole, 5-(1-methylethenyl)-Yield 109.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

14.52 g of 2-(1,3-benzodioxol-5-yl)-2-propanol was dissolved in 200 ml of benzene, followed by the addition of a catalytic amount of p-toluenesulfonic acid monohydrate. The obtained mixture was heated under reflux in a short-neck Kieldahl flask fitted with a Dean-Stark reflux condenser for 2.5 hours. The reaction mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of common salt successively, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated to obtain 14.33 g of the title compound as an oil.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux in a short-neck Kieldahl flask
  3. customfitted with a Dean-Stark
  4. temperaturereflux condenser for 2.5 hours
  5. washThe reaction mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate
  6. dry with materiala saturated aqueous solution of common salt successively, dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9c5ed5fbc7a44ba582fe1183230aba21
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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