Water → methyl (E,E)-4-methyl-2,4-octadienoate

HRID 2396923Notes

Reaction equation

HRID 2396923 reaction equation
[CH3:1][O-].[Na+].[CH2:4]([O:6][C:7](=[O:17])[C:8]([CH2:15][CH3:16])(CC)P(O)(O)=O)C.[CH3:18]/[C:19](=[CH:22]\[CH2:23]CC)/C=O.O>CO>[CH3:1]/[C:16](=[CH:18]\[CH2:19][CH2:22][CH3:23])/[CH:15]=[CH:8]/[C:7]([O:6][CH3:4])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 53645342-Methyl-2-hexenalHCID 10942334Sodium MethoxideHCID 17846631Ethyl diethyl-phosphonoacetate

Product 1

HCID 12700340methyl (E,E)-4-methyl-2,4-octadienoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 28 wt % solution of sodium methoxide in methanol (112.6 g) at 10° C. were added dropwise diethyl phosphonoacetic acid ethyl ester (110.75 g) and (E)-2-methyl-2-hexenal (50.36 g) successively under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 4 hours, poured into chilled water and extracted with dichloromethane. The extract was washed with brine, dried over anhydrous magnesium sulfate, and evaporated to give 74.88 g of crude methyl (E,E)-4-methyl-2,4-octadienoate as an oil. This oil was used in the next reaction without further purification.

Workup

  1. additionpoured
  2. extractionextracted with dichloromethane
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-b7c77086d49a4130bddc33484b53f015
Source dataset
uspto-grants-1996_02
Patent number
US05495023

Reaction notes

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