p-Toluenesulfonic acid → HCID 54413729, compound

HRID 2290816Notes

Reaction equation

HRID 2290816 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH:31]2[O:36]CCO[CH2:32]2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31](=[O:36])[CH3:32])[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 70452497HCID 70452497, compound

Product 1

HCID 54413729HCID 54413729, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.4 g of 1-(3,4-dibenzyloxyphenyl)-9-ethylenedioxy-1-decene, 50 ml of acetone, and 50 mg of p-toluenesulfonic acid was stirred overnight at room temperature. After adding thereto 50 mg of sodium carbonate, the reaction mixture was concentrated under reduced pressure, and after adding thereto 50 ml of water, the product was extracted with toluene. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to provide 1.1 g of 1-(3,4-dibenzyloxyphenyl)-1-decen-9-one as an oil.

Workup

  1. additionAfter adding
  2. concentration50 mg of sodium carbonate, the reaction mixture was concentrated under reduced pressure
  3. additionafter adding
  4. extraction50 ml of water, the product was extracted with toluene
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3febb1298e00424fa4edf85853263a03
Source dataset
uspto-grants-1986_10
Patent number
US04618627

Reaction notes

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