Water → 3-Methoxy-2-(5-hexenyl)acrolein

HRID 622279Notes

Reaction equation

HRID 622279 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S(O)(=O)=O)=[CH:4][CH:3]=1.[C:13](=[O:16])([O-])O.[Na+].[CH2:18]([O:20][CH2:21]C)C>>[CH3:18][O:20][CH:21]=[C:12]([CH2:2][CH2:7][CH2:6][CH2:5][CH:4]=[CH2:3])[CH:13]=[O:16]

Participants

5

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 538716643-Methoxy-2-(5-hexenyl)acrolein

Procedure

A mixture of 3.77 g of crude (5-hexenyl)malon-tetraacetal, 0.35 ml of water and 15 mg of p-toluene-sulphonic acid is heated to 80°-85° C. for 3 hours while stirring. After cooling the mixture is treated with 160 mg of sodium hydrogen carbonate and stirred for 1.5 hours. Subsequently, the reaction mixture is diluted with diethyl ether, extracted three times with cold 3N sodium hydroxide solution, washed with water and dried. The crude 3-methoxy-2-(5-hexenyl)acrolein which is obtained after evaporation of the solvent is further processed without additional purification.

Workup

  1. temperatureis heated to 80°-85° C. for 3 hours
  2. temperatureAfter cooling the mixture
  3. stirringstirred for 1.5 hours
  4. extractionextracted three times with cold 3N sodium hydroxide solution
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-7a16b2e042c946bc855ab4c0865a5862
Source dataset
uspto-grants-1988_09
Patent number
US04770503

Reaction notes

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