Hydrochloric Acid → HCID 13882782, compound

HRID 1032640Notes

Reaction equation

HRID 1032640 reaction equation
[CH2:1]([O:19][C:20]1[C:21]([O:23][C@H:24]([C@H:27]([CH2:29][OH:30])[OH:28])[C:25]=1[OH:26])=[O:22])[CH2:2][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][CH3:18].N1C=CC=CC=1.[C:37](Cl)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.Cl>C(Cl)(Cl)Cl>[C:37]([O:26][C:25]1[C@@H:24]([C@H:27]([CH2:29][OH:30])[OH:28])[O:23][C:21](=[O:22])[C:20]=1[O:19][CH2:1][CH2:2][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][CH3:18])(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7412Benzoyl chlorideHCID 54694681HCID 54694681, compound

Product 1

HCID 13882782HCID 13882782, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-O-octadecyl-L-ascorbic acid (0.8 g, 2 mmole) in chloroform (20 ml) was added pyridine (1 ml), followed by adding dropwise benzoyl chloride (0.28 g, 2 mmole) at room temperature. The reaction mixture was stirred for one hour, to which was added 2N hydrochloric acid to acidify it. The organic layer was washed with water and dried (over magnesium sulfate). The solvent was evaporated off, and the product was recrystallized from isopropyl ether-ethyl acetate to give 3-O-benzoyl-2-O-octadecyl-L-ascorbic acid (0.6 g, 49%), m.p. 68°-69° C. C3H48O7 (Found: C,69.94; H,8.98%. Anal. Calcd: C,69.89; H,9.08)

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried (over magnesium sulfate)
  3. customThe solvent was evaporated off
  4. customthe product was recrystallized from isopropyl ether-ethyl acetate

Sources & evidence

ORD record
ord-a3f2ea8f39864103a9bbc78bdc53bb8c
Source dataset
uspto-grants-1990_09
Patent number
US04959362

Reaction notes

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