HCID 13882790, compound → HCID 54694681, compound

HRID 868692Notes

Reaction equation

HRID 868692 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 at 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 (1.5 g). m.p. 127°-128° C.

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-e7d610f850a64e1cb3eadd22c4d9a2b2
Source dataset
uspto-grants-1988_10
Patent number
US04780549

Reaction notes

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