p-Toluenesulfonic acid → HCID 54481677, compound

HRID 1980396Notes

Reaction equation

HRID 1980396 reaction equation
[CH2:1]([O:3][C:4](OCC)([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[CH2:5][CH3:6])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH3:6])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 56637922HCID 56637922, compound

Product 1

HCID 54481677HCID 54481677, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

103.3 g of p-methoxy-propiophenone diethyl ketal are treated with 1.1 g of p-toluenesulphonic acid and heated in a distillation apparatus to 140° C. (oil bath temperature). In so doing, the ethanol formed is distilled off continuously at atmospheric pressure. 20 g of ethanol are distilled off within 31/2 hours. Subsequently, the mixture remaining is distilled in a high vacuum over a 15 cm column. There are obtained 62.2 g of 1-(p-methoxyphenyl)-1-ethoxy-1-propene (yield: 74.8% of theory). B.p.=78°-79° C. 0.3 mmHg; nD20 =1.5315: d420 =1.0175.

Workup

  1. distillationis distilled off continuously at atmospheric pressure
  2. distillation20 g of ethanol are distilled off within 31/2 hours
  3. distillationSubsequently, the mixture remaining is distilled in a high vacuum over a 15 cm column

Sources & evidence

ORD record
ord-e5b833ce4015492aab9771e614840016
Source dataset
uspto-grants-1985_04
Patent number
US04508925

Reaction notes

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