Cyclopropanecarboxaldehyde → Cyclopropanecarboxaldehyde

HRID 2260032Notes

Reaction equation

HRID 2260032 reaction equation
[CH:1]1([CH:4]=[O:5])[CH2:3][CH2:2]1>[Pd]>[CH:1]1([CH:4]=[O:5])[CH2:3][CH2:2]1.[CH:4](=[O:5])/[CH:1]=[CH:2]/[CH3:3]

Participants

4

Conditions

Temperature
60 °C

Procedure

To a glass liner with a magnetic stirrer were charged 0.7 g of 5% palladium on carbon catalyst and 7 g of cyclopropanecarboxaldehyde (94% assay, containing 6% crotonaldehyde). The glass liner was placed in a 250 ml autoclave and purged with nitrogen then with hydrogen. The autoclave was pressurized to 42.4 bar absolute with hydrogen and heated to 60° C. The mixture was stirred under these conditions for 16 hours. The reactor was cooled and vented with nitrogen and the catalyst was removed by filtration. GC analysis of the crude mixture showed that n-butanol was the only product obtained (100% over reduction of cyclopropanecarboxaldehyde and crotonaldehyde). Cyclopropylmethanol was not detected.

Workup

  1. custompurged with nitrogen
  2. temperatureThe reactor was cooled
  3. customthe catalyst was removed by filtration

Sources & evidence

ORD record
ord-718c23ad3e3248218faef828425e8b87
Source dataset
uspto-grants-1995_12
Patent number
US05475151

Reaction notes

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