HCID 20322222, compound → HCID 20322202, compound

HRID 839975Notes

Reaction equation

HRID 839975 reaction equation
C([O:8][CH2:9][CH2:10][C:11]([CH:13]([CH2:23][CH2:24][CH2:25][CH:26]([O:32]CC1C=CC=CC=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[O:12])C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[OH:8][CH2:9][CH2:10][C:11]([CH:13]([CH2:23][CH2:24][CH2:25][CH:26]([OH:32])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[O:12]

Participants

5

Reactant 2

HCID 20322222HCID 20322222, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20322202HCID 20322202, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A magentically stirred solution of 8-(3-benzyloxypropionyl)-12-benzyloxyheptadecanoic acid (2.37 g., 4.4 millimole) in ethanol (50 ml.) is subjected to hydrogenation at atmospheric pressure at 23° C. in the presence of a 10% palladium on charcoal catalyst (0.3 g.) for one hour. The hydrogen uptake is 2.4 ml. (100% theory). The catalyst is removed by filtration and the solvent is removed by evaporation in vacuo to give 8-(3-hydroxypropionyl)-12-hydroxyheptadecanoic acid . 1/3 chloroformate as a viscous, colorless liquid (1.55 g., 97% yield); pmr (CDCl3) δ 0.88 (3H,t), 2.03 (H,m), 2.32 (2H,t), 2.68 (2H,t, J=5.5 cps.), 3.65 (H, b.s.), 3.86 (2H,t, J=5.5 cps.), 5.50 (3H, exchangeable s) and 7.32 (1/3H,s).

Workup

  1. customThe catalyst is removed by filtration
  2. customthe solvent is removed by evaporation in vacuo

Sources & evidence

ORD record
ord-382ebf9a675b46da8b6df55d7b8bf736
Source dataset
uspto-grants-1978_06
Patent number
US04097504

Reaction notes

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