Methyl acetoacetate → HCID 86734326, compound

HRID 1974172Notes

Reaction equation

HRID 1974172 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[Na].[CH2:10]([O:28][C:29]1[O:33][CH:32]=[C:31]([C:34](Cl)=[O:35])[CH:30]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C1C=CC=CC=1>[CH2:10]([O:28][C:29]1[O:33][CH:32]=[C:31]([C:34]([CH:2]([C:3]([CH3:5])=[O:4])[C:1]([O:7][CH3:8])=[O:6])=[O:35])[CH:30]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 5360545SodiumHCID 86734325HCID 86734325, compound

Product 1

HCID 86734326HCID 86734326, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a cooled mixture of 40.0 g (0.106 mole) of 5-(cis-9-octadecen-1-yloxy)-3-furoic acid in methylene chloride is added 30 ml of thionyl chloride. The mixture is stirred for 5 hours. Then the solvent and excess thionyl chloride is removed under reduced pressure affording the crude 5-(cis-9-octadecen-1-yloxy)-3-furoyl chloride. A mixture of 11.6 g (0.100 moles) of methyl acetoacetate and 2.3 g of sodium in 1 liter of benzene is refluxed for 20 hours, then cooled, and the crude 5-(cis-9-octadecen-1-yloxy)-3-furoyl chloride is added over a two hour period. The mixture is refluxed for 6 hours, cooled by the addition of ice and mixed well. The benzene layer is separated, washed with 5% sodium bicarbonate solution and dried. The benzene is distilled off under reduced pressure yielding 2-[5-(cis-9-octadecen-1-yloxy)-3-furoyl]acetoacetic acid, methyl ester. To a solution of 3.3 g of ammonium chloride in 15 ml of water at 40° C is added 10 g of the above ester maintaining the temperature at 40° C for 15 minutes followed by rapid cooling. The solution is extracted with ether, the extract dried, and evaporated to dryness affording 2-[5-(cis-9-octadecen-1-yloxy)-3-furoyl]acetic acid methyl ester.

Workup

  1. temperatureis refluxed for 20 hours
  2. temperaturecooled
  3. temperatureThe mixture is refluxed for 6 hours
  4. temperaturecooled by the addition of ice
  5. additionmixed well
  6. customThe benzene layer is separated
  7. washwashed with 5% sodium bicarbonate solution
  8. customdried
  9. distillationThe benzene is distilled off under reduced pressure

Sources & evidence

ORD record
ord-e162c31c99354831b58892e67bcc8e7e
Source dataset
uspto-grants-1976_12
Patent number
US04000164

Reaction notes

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