Formaldehyde → 2-Cyclohexylprop-2-en-1-al

HRID 634977

Reaction equation

HRID 634977 reaction equation
S(=O)(=O)(O)O.C=O.[CH:8]1([CH2:14][CH:15]=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[CH2:17](NCC)C>>[CH:8]1([C:14](=[CH2:17])[CH:15]=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 8021DiethylamineHCID 3166272-Cyclohexylacetaldehyde

Product 1

HCID 125770702-Cyclohexylprop-2-en-1-alYield 81%

Conditions

Temperature
80 °C

Procedure

Successively, sulfuric acid 62% (79.4 g, 0.5 mol), aqueous formaldehyde 35% (82 g, 1.0 mol) and cyclohexyl acetaldehyde (100.8 g, 0.8 mol) were added slowly to diethylamine (73 g, 1.0 mol) at 0° C. After stirring at 80° C. overnight, the reaction mixture was extracted with MTBE. The combined organic phases were washed with H2O until neutral pH was achieved, dried (MgSO4) and concentrated in vacuo. The crude product was distilled under reduced pressure using a Widmer column (10 Torr, 80° C.) yielding 89.5 g (81%) of pure product as colorless oil.

Workup

  1. extractionthe reaction mixture was extracted with MTBE
  2. washThe combined organic phases were washed with H2O until neutral pH
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. distillationThe crude product was distilled under reduced pressure
  6. customa Widmer column (10 Torr, 80° C.)

Sources & evidence

ORD record
ord-7a4e627e30f7477b81179cf836b5d1b1
Source dataset
uspto-grants-2001_02
Patent number
US06184419B2

Linked notes

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