Ammonium Chloride → HCID 68142135, compound

HRID 1974173Notes

Reaction equation

HRID 1974173 reaction equation
[Cl-].[NH4+].[CH2:3]([O:21][C:22]1[O:26][CH:25]=[C:24]([C:27]([CH:29](C(C)=O)[C:30]([O:32][CH3:33])=[O:31])=[O:28])[CH:23]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>O>[CH3:33][O:32][C:30](=[O:31])[CH2:29][C:27]([C:24]1[CH:23]=[C:22]([O:21][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[O:26][CH:25]=1)=[O:28]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 86734326HCID 86734326, compound

Product 1

HCID 68142135HCID 68142135, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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. extractionThe solution is extracted with ether
  2. customthe extract dried
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-d9eb135f562c4678924e15437c157e51
Source dataset
uspto-grants-1976_12
Patent number
US04000164

Reaction notes

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