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

HRID 2295024Notes

Reaction equation

HRID 2295024 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](=C\CC)/[CH:20]=O.O>CO.O1CCCC1>[CH3:1]/[C:16](=[CH:18]\[CH2:19][CH3:20])/[CH:15]=[CH:8]/[C:7]([O:6][CH3:4])=[O:17]

Participants

7

Reactant 4

HCID 962WaterHCID 5319754(E)-2-Methyl-2-pentenalHCID 10942334Sodium MethoxideHCID 17846631Ethyl diethyl-phosphonoacetate

Product 1

HCID 12791883methyl (E,E)-4-methyl-2,4-heptadienoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 28 wt % solution of sodium methoxide in methanol (226 g) at 20° C. was added dropwise diethyl phosphonoacetic acid ethyl ester (239.8 g). The solution was stirred at the same temperature for 30 minutes under a nitrogen atmosphere. A solution of (E)-2-methyl-2-pentenal (100 g) in tetrahydrofuran (200 ml) was added dropwise at 20° C. during 20 minutes and the solution was stirred for 1 hour. The reaction mixture was poured into chilled water and extracted twice with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give methyl (E,E)-4-methyl-2,4-heptadienoate (169.2 g) as an oil. This oil was used in the next reaction without further purification.

Workup

  1. stirringthe solution was stirred for 1 hour
  2. additionThe reaction mixture was poured
  3. extractionextracted twice with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-e877bad08d304bad8d2b34830a77025b
Source dataset
uspto-grants-1997_11
Patent number
US05691366

Reaction notes

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