Hydrochloric Acid → HCID 19900623, compound

HRID 1029979Notes

Reaction equation

HRID 1029979 reaction equation
[C:1](=[O:42])([O:11][C:12]1[C:13]([CH3:41])=[C:14]2[C:19](=[C:20]([CH3:23])[C:21]=1[CH3:22])[O:18][C:17]([CH3:40])([CH2:24][CH2:25][CH2:26][CH:27]([CH3:39])[CH2:28][CH2:29][CH2:30][CH:31]([CH3:38])[CH2:32][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:16][CH2:15]2)[O:2][CH2:3][CH:4]1[CH2:8][O:7]C(C)(C)[O:5]1.O1CCCC1.CO.Cl>CCOCC>[C:1](=[O:42])([O:11][C:12]1[C:13]([CH3:41])=[C:14]2[C:19](=[C:20]([CH3:23])[C:21]=1[CH3:22])[O:18][C:17]([CH3:40])([CH2:24][CH2:25][CH2:26][CH:27]([CH3:39])[CH2:28][CH2:29][CH2:30][CH:31]([CH3:38])[CH2:32][CH2:33][CH2:34][CH:35]([CH3:36])[CH3:37])[CH2:16][CH2:15]2)[O:2][CH2:3][CH:4]([OH:5])[CH2:8][OH:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8028TetrahydrofuranHCID 19900633HCID 19900633, compound

Product 1

HCID 19900623HCID 19900623, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture comprising 3.9 g of 2,2-dimethyl-1,3-dioxolan-4-ylmethyl 2,5,7,8-tetramethyl-2-(4',8',12'-trimethyltridecyl)-6-chromanyl carbonate, 15 ml of tetrahydrofuran, 5 ml of methanol and 5 ml of 2 N hydrochloric acid was stirred and heated under reflux for 3 hours. The reaction mixture was dissolved in ether, successively washed with water, an aqueous solution of sodium hydrogencarbonate and water, and dried over magnesium sulfate. 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 3.3 g of the title compound as a pale yellow, viscous liquid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. washsuccessively washed with water
  4. dry with materialan aqueous solution of sodium hydrogencarbonate and water, and dried over magnesium sulfate
  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-b5f9849347f04d4b8219aed84ccf7448
Source dataset
uspto-grants-1992_04
Patent number
US05102895

Reaction notes

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