p-Toluenesulfonic acid monohydrate → HCID 54179385, compound

HRID 1284170Notes

Reaction equation

HRID 1284170 reaction equation
O[CH:2]([C:13]1[CH:18]=[CH:17][C:16]2[O:19][CH2:20][O:21][C:15]=2[CH:14]=1)[CH2:3][CH2:4][CH:5]([CH3:12])[CH2:6][CH2:7][O:8][CH:9]([CH3:11])[CH3:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH:9]([O:8][CH2:7][CH2:6][CH:5]([CH3:12])[CH2:4][CH:3]=[CH:2][C:13]1[CH:18]=[CH:17][C:16]2[O:19][CH2:20][O:21][C:15]=2[CH:14]=1)([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21515711HCID 21515711, compound

Product 1

HCID 54179385HCID 54179385, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

6.50 g (0.022 mol) of 1-(1-hydroxy-6-isopropoxy-4-methyl-hexyl)-3,4-methylenedioxybenzene are boiled at reflux together with 0.30 g (0.0016 mol) of p-toluenesulphonic acid monohydrate in 500 cc of benzene over the course of 2 hours and using a Dean-Stark trap. After cooling to room temperature, the benzene solution is washed with saturated sodium bicarbonate solution, water and saturated sodium chloride solution, dried with sodium sulphate and evaporated in a vacuum. After chromatography of the residue on silica gel wth hexane/ethyl acetate (98:2), pure 1-(6-isopropoxy-4-methyl-1-hexenyl)-3,4-methylenedioxybenzene is obtained as a colourless oil. nD20 = 1.5258.

Workup

  1. washthe benzene solution is washed with saturated sodium bicarbonate solution, water and saturated sodium chloride solution
  2. dry with materialdried with sodium sulphate
  3. customevaporated in a vacuum

Sources & evidence

ORD record
ord-0b0af828555941e0b8a758d869456734
Source dataset
uspto-grants-1976_08
Patent number
US03978097

Reaction notes

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