Diethyl Ether → HCID 86734065, compound

HRID 1287551Notes

Reaction equation

HRID 1287551 reaction equation
N1[CH2:6][CH2:5]CCC1.[CH2:7]([SH:19])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH:20](=[O:24])/C=C/C.[CH2:25](OCC)C>>[CH2:9]([CH:8]([CH3:25])[CH:7]([SH:19])[CH:20]=[O:24])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:5][CH3:6]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 8082PiperidineHCID 81951-DodecanethiolHCID 447466Crotonaldehyde

Product 1

HCID 86734065HCID 86734065, compoundYield 90%

Conditions

Temperature
10 °C

Procedure

0.02 gm Piperidine (catalyst) was dissolved in 30 ml diethyl ether, 0.5 mole lauryl mercaptan was added and the mixture was cooled to 10° C. To this mixture was added 0.5 mole of crotonaldehyde, the rate of addition being such that the reaction temperature never exceeded 10° C. After the addition was completed, the reaction mixture was maintained at a temperature of less than 10° C for a further 60 hours. The reaction mixture was kept under a blanket of nitrogen throughout the preparation. The product β-lauryl-mercaptobutyraldehyde was then obtained by distillation of the mixture under reduced pressure, the product being the fraction of boiling point 154°-155° C at 3 mm Hg pressure. The yield was 90%.

Workup

  1. additionthe rate of addition
  2. custombeing such that the reaction temperature never exceeded 10° C
  3. additionAfter the addition
  4. temperaturethe reaction mixture was maintained at a temperature of less than 10° C for a further 60 hours
  5. customThe reaction mixture was kept under a blanket of nitrogen throughout the preparation

Sources & evidence

ORD record
ord-ebc7ee88cfea47c09361971abc68e60d
Source dataset
uspto-grants-1976_10
Patent number
US03985710

Reaction notes

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