HCID 13882790, compound → HCID 54694681, compound

HRID 1032641Notes

Reaction equation

HRID 1032641 reaction equation
C([O:8][C:9]1[C@@H:14]([C@H:15]([CH2:17][OH:18])[OH:16])[O:13][C:11](=[O:12])[C:10]=1[O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[CH2:20]([O:19][C:10]1[C:11]([O:13][C@H:14]([C@H:15]([CH2:17][OH:18])[OH:16])[C:9]=1[OH:8])=[O:12])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

4

Reactant 1

HCID 13882790HCID 13882790, compound

Product 1

HCID 54694681HCID 54694681, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-O-Benzyl-2-O-octadecylascorbic acid (2.1 g) was dissolved in ethyl acetate (25 ml), and 5% Pd-C (0.5 g) was added to the solution to conduct catalytic reduction under atmospheric pressure. The catalyst was filtered out, and the filtrate was concentrated under reduced pressure. The reaction product was recrystallized from isopropyl ether-ethyl acetate to give 2-O-octadecylascorbic acid [compound (1-12)](1.5 g).

Workup

  1. filtrationThe catalyst was filtered out
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe reaction product was recrystallized from isopropyl ether-ethyl acetate

Sources & evidence

ORD record
ord-4d2e758d126a47be83928c80ae64da7f
Source dataset
uspto-grants-1990_09
Patent number
US04959362

Reaction notes

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