HCID 53696590, compound → Methyl 18-methyleicosanoate

HRID 2260073Notes

Reaction equation

HRID 2260073 reaction equation
[CH3:1][CH:2]([CH2:23][CH3:24])[CH:3]=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20].[H][H]>[Pt]=O.C(O)(=O)C>[CH3:1][CH:2]([CH2:23][CH3:24])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 2

HCID 53696590HCID 53696590, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11221509Methyl 18-methyleicosanoateYield 56.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

5.3 gm of methyl 18-methyl-16-eicosenoate charged into an autoclave together with 0.3 gm of platinum oxide and 30 ml of acetic acid were reduced under 100 atm hydrogen pressure at 100° C. for 5 hours. After the reaction, the catalyst was removed by filtration and the solvent was evaporated to obtain 3 gm of methyl 18-methyleicosanoate, which was purified by flash column chromatography (chloroform). The product was dissolved into 150 ml of a 5% sodium hydroxide-ethanol solution and stirred at room temperature for 8 hours. Then, 95 ml of 2N sulfuric acid was added to obtain a solid. The solid material was filtered and washed with water to obtain 3.1 gm of 18-methyleicosanoic acid (yield: 59% from methyl 18-methyl-16-eicosenoate).

Workup

  1. customAfter the reaction
  2. customthe catalyst was removed by filtration
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7da4b0feea0b4eca87680c7153e26bee
Source dataset
uspto-grants-1995_12
Patent number
US05476649

Reaction notes

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