Hydrochloric Acid → HCID 19900613, compound

HRID 1029981Notes

Reaction equation

HRID 1029981 reaction equation
[C:1](=[O:43])([O:12][C:13]1[C:14]([CH3:42])=[C:15]2[C:20](=[C:21]([CH3:24])[C:22]=1[CH3:23])[O:19][C:18]([CH3:41])([CH2:25][CH2:26][CH2:27][CH:28]([CH3:40])[CH2:29][CH2:30][CH2:31][CH:32]([CH3:39])[CH2:33][CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[CH2:17][CH2:16]2)[O:2][CH2:3][CH2:4][CH:5]1[CH2:9][O:8]C(C)(C)[O:6]1.O1CCCC1.CO.Cl>CCOCC>[C:1](=[O:43])([O:12][C:13]1[C:14]([CH3:42])=[C:15]2[C:20](=[C:21]([CH3:24])[C:22]=1[CH3:23])[O:19][C:18]([CH3:41])([CH2:25][CH2:26][CH2:27][CH:28]([CH3:40])[CH2:29][CH2:30][CH2:31][CH:32]([CH3:39])[CH2:33][CH2:34][CH2:35][CH:36]([CH3:37])[CH3:38])[CH2:17][CH2:16]2)[O:2][CH2:3][CH2:4][CH:5]([OH:6])[CH2:9][OH:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8028TetrahydrofuranHCID 21685081HCID 21685081, compound

Product 1

HCID 19900613HCID 19900613, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture comprising 5.0 g of 2,2-dimethyl-1,3-dioxolan-4-yiethyl 2,5,7,8-tetramethyl-2-(4',8', 12'-trimethyltridecyl)-6-chromanyl carbonate, 20 ml of tetrahydrofuran, 10 ml of methanol and 8 ml of 2N hydrochloric acid was heated under reflux for 3 hours with stirring. Then the reaction mixture was dissolved in ether, successively washed with water, an aqueous solution of sodium hydrogencarbonate and water, and dried. After distilling off the solvent, the obtained oily residue was purified by column chromatography (silica gel, hexane : ethyl acetate=3.5:1.5) to thereby give 4.2 g of the title compound as a pale yellow, viscous liquid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. washsuccessively washed with water
  4. dry with materialan aqueous solution of sodium hydrogencarbonate and water, and dried
  5. distillationAfter distilling off the solvent
  6. customthe obtained oily residue was purified by column chromatography (silica gel, hexane : ethyl acetate=3.5:1.5)

Sources & evidence

ORD record
ord-d6c6b92591d546a5b8fd9babaa68f574
Source dataset
uspto-grants-1992_04
Patent number
US05102895

Reaction notes

Loading…