Dimethyl malonate → HCID 54377802, compound

HRID 325132

Reaction equation

HRID 325132 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 54377802HCID 54377802, compoundYield 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-c1c18be20e8b487fb1171076433c2256
Source dataset
uspto-grants-2001_04
Patent number
US06222062B1

Linked notes

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