2,6-Dimethyl-5,6-dihydro-2H-thiopyran-3-carbaldehyde → HCID 20225470, compound

HRID 1249254Notes

Reaction equation

HRID 1249254 reaction equation
[CH:1]([C:3]1[CH:4]([CH3:10])[S:5][CH:6]([CH3:9])[CH2:7][CH:8]=1)=[O:2]>[Ni].C(OCC)(=O)C>[CH:1]([CH:3]1[CH2:8][CH2:7][CH:6]([CH3:9])[S:5][CH:4]1[CH3:10])=[O:2]

Participants

4

Conditions

Temperature
90 °C

Procedure

100 g of 3-formyl-5,6-dihydro-2,6-dimethyl-2H-thiopyran prepared as described in Example 11(a), 60 ml of ethyl acetate and 30 g of Raney nickel were introduced into a stirred autoclave having a capacity of 300 ml. The autoclave was closed, and flushed with nitrogen. Hydrogen was forced in until the total pressure reached 30 bar, after which the mixture was heated to 90° C. and hydrogenated under these conditions until the pressure remained constant. It was then cooled, the catalyst was filtered off and the filtrate was purified by distillation under reduced pressure. 89 g (88% of theory) of 3-formyl-2,6-dimethyltetrahydrothiopyran of boiling point 127°-129° C./10 mbar were obtained.

Workup

  1. additionwere introduced into a stirred autoclave
  2. customThe autoclave was closed
  3. customflushed with nitrogen
  4. temperatureIt was then cooled
  5. filtrationthe catalyst was filtered off
  6. distillationthe filtrate was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-aae7d5740c6e4573951ade0dc9bfa76c
Source dataset
uspto-grants-1986_12
Patent number
US04629799

Reaction notes

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