2-Methylenehexanal → HCID 14640309, compound

HRID 1007665Notes

Reaction equation

HRID 1007665 reaction equation
[Na+].[C:2]1([CH3:11])[CH:7]=[CH:6][C:5]([S:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH2:12]([C:16](=[CH2:19])[CH:17]=[O:18])[CH2:13][CH2:14][CH3:15]>C(O)(=O)C.O>[CH3:11][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:19][CH:16]([CH2:12][CH2:13][CH2:14][CH3:15])[CH:17]=[O:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 706122-MethylenehexanalHCID 2723791Sodium p-toluenesulfinate

Product 1

HCID 14640309HCID 14640309, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 4-toluenesulfinate sodium salt (10.10 g, 56.68 mmol) in 35 mL of acetic acid at 50° C. is added 2-butylacrolein (10.6 mL, 79.66 mmol) slowly. The reaction mixture is kept at 50° C. for 3 hours. After cooling to room temperature, the mixture is diluted with 50 mL of water and extracted with ethyl acetate (2×25 mL). The combined extract is washed with saturated NaHCO3, water, brine, and dried with MgSO4. After removing solvents, the product is obtained as a yellow liquid in 75% yield.

Workup

  1. extractionextracted with ethyl acetate (2×25 mL)
  2. extractionThe combined extract
  3. washis washed with saturated NaHCO3, water, brine
  4. dry with materialdried with MgSO4
  5. customAfter removing solvents
  6. customthe product is obtained as a yellow liquid in 75% yield

Sources & evidence

ORD record
ord-de77ab2c8e6544b88756a99c8ec3b0c3
Source dataset
uspto-grants-2004_09
Patent number
US06794544B2

Reaction notes

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