p-Toluenesulfonic acid monohydrate → HCID 53665079, compound

HRID 1284171Notes

Reaction equation

HRID 1284171 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O[CH:14]([C:25]1[CH:30]=[CH:29][C:28]2[O:31][CH2:32][O:33][C:27]=2[CH:26]=1)[CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23]>C1C=CC=CC=1>[CH2:20]([O:19][CH2:18][CH2:17][CH2:16][CH:15]=[CH:14][C:25]1[CH:30]=[CH:29][C:28]2[O:31][CH2:32][O:33][C:27]=2[CH:26]=1)[CH2:21][CH:22]([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21515693HCID 21515693, compound

Product 1

HCID 53665079HCID 53665079, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

0.07 g (0.37 millimol) of p-toluenesulphonic acid-monohydrate are added to 2.2g (0.0075 mol) of 1-(1-hydroxy-5-isopentyloxy-pentyl)-3,4-methylenedioxybenzene, dissolved in 150 cc of benzene. The solution is rapidly heated to boiling temperature and boiled at reflux over the course of 20 minutes and using a DeanStark-trap. After cooling, the benzene solution is extracted with saturated sodium bicarbonate solution, subsequently with water and saturated sodium chloride solution and dried with sodium sulphate. The solution is evaporated and the residue chromatographed on silica gel with hexane/ethyl acetate (97:3), whereupon the 1-(5-isopentyloxy-1-pentenyl)-3,4-methylenedioxybenzene is obtained as a pure, colourless oil. nD20 = 1.5248

Workup

  1. temperatureThe solution is rapidly heated
  2. temperatureat reflux over the course of 20 minutes
  3. temperatureAfter cooling
  4. extractionthe benzene solution is extracted with saturated sodium bicarbonate solution, subsequently with water and saturated sodium chloride solution
  5. dry with materialdried with sodium sulphate
  6. customThe solution is evaporated
  7. customthe residue chromatographed on silica gel with hexane/ethyl acetate (97:3), whereupon the 1-(5-isopentyloxy-1-pentenyl)-3,4-methylenedioxybenzene
  8. customis obtained as a pure, colourless oil

Sources & evidence

ORD record
ord-509cfe40b29244c9b53d1d46dbf823bf
Source dataset
uspto-grants-1976_08
Patent number
US03978097

Reaction notes

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