Dimethyl malonate → Malonic acid didec-9-enyl ester

HRID 1699993Notes

Reaction equation

HRID 1699993 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].C(O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19].C[O-].[Na+]>CO>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][C:1]([O:8][CH2:9][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19])=[O:7])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=[CH2:11]

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 256129-Decen-1-olHCID 10942334Sodium Methoxide

Product 1

HCID 54377802Malonic acid didec-9-enyl esterYield 59.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 150 g dimethyl malonate and 464 g dec-9-en-1-ol, 30 g sodium methoxide (5.4 M in methanol) was dropped in. The mixture was heated to 120° C. to and the methanol formed was distilled off. After 6 hours, the mixture was cooled down, diluted with ether and washed with HCl 2N, saturated sodium bicarbonate and water. The organic phase was dried, filtered and evaporated to dryness. The resulting yellow oil was purified by distillation to yield 258 g of a yellow oil.

Workup

  1. additionwas dropped in
  2. customformed
  3. distillationwas distilled off
  4. temperaturethe mixture was cooled down
  5. additiondiluted with ether
  6. washwashed with HCl 2N, saturated sodium bicarbonate and water
  7. customThe organic phase was dried
  8. filtrationfiltered
  9. customevaporated to dryness
  10. distillationThe resulting yellow oil was purified by distillation

Sources & evidence

ORD record
ord-5abe08bf16114696831d47de8f375856
Source dataset
uspto-grants-2002_02
Patent number
US06348618B1

Reaction notes

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