Formaldehyde → HCID 44542715, compound

HRID 2361563Notes

Reaction equation

HRID 2361563 reaction equation
[CH3:1]/[CH:2]=[CH:3]/[CH:4]=[O:5].[CH3:6][C:7]([CH:9]=[CH:10]C)=[CH2:8].C=O.O.N1CC[CH2:17][CH2:16]1.C(O)(=O)CC>C([O-])(O)=O.[Na+]>[CH3:1][CH:2]1[CH:8]=[C:7]([CH3:6])[CH2:9][CH2:10][C:3]1([CH:16]=[CH2:17])[CH:4]=[O:5]

Participants

8

Reactant 6

HCID 712FormaldehydeHCID 962WaterHCID 1032Propionic AcidHCID 142381,3-Pentadiene, 2-methyl-HCID 31268PyrrolidineHCID 447466Crotonaldehyde

Product 1

HCID 44542715HCID 44542715, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of crotonic aldehyde (165.2 g, 2.36 mol), 2-methyl-penta-1,3-diene (361.6 g, 4.41 mol) and formalin (37% in water (200 g, 2.46 mol) was added a mixture of pyrrolidine (16.0 g, 0.22 mol) and propionic acid (17.0 g, 0.23 mol). The mixture was placed in an autoclave and heated to 60-100° C. for 8 h. The reaction mixture was cooled to room temperature, diluted with sat. NaHCO3 and extracted 3 times with MTBE (200 ml). The combined org. layers were washed with brine (200 ml), dried (MgSO4) and evaporated in vacuo. The residue was purified by distillation to give 2,4-dimethyl-1-vinylcyclohex-3-enecarbaldehyde (50% yield). Boiling point: 50-53° C./0.15 mbar.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted 3 times with MTBE (200 ml)
  4. washlayers were washed with brine (200 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. distillationThe residue was purified by distillation

Sources & evidence

ORD record
ord-a65998b2c4db406ab5b0fa20c7e6bdd5
Source dataset
uspto-grants-2014_04
Patent number
US08691746B2

Reaction notes

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