Water → HCID 21685075, compound

HRID 1029988Notes

Reaction equation

HRID 1029988 reaction equation
[C:1](=[O:53])([O:22][C:23]1[C:24]([CH3:52])=[C:25]2[C:30](=[C:31]([CH3:34])[C:32]=1[CH3:33])[O:29][C:28]([CH3:51])([CH2:35][CH2:36][CH2:37][CH:38]([CH3:50])[CH2:39][CH2:40][CH2:41][CH:42]([CH3:49])[CH2:43][CH2:44][CH2:45][CH:46]([CH3:48])[CH3:47])[CH2:27][CH2:26]2)[O:2][CH2:3][CH2:4][CH:5]([CH2:14][O:15]C1CCCCO1)[CH2:6][O:7]C1CCCCO1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>CO>[C:1](=[O:53])([O:22][C:23]1[C:24]([CH3:52])=[C:25]2[C:30](=[C:31]([CH3:34])[C:32]=1[CH3:33])[O:29][C:28]([CH3:51])([CH2:35][CH2:36][CH2:37][CH:38]([CH3:50])[CH2:39][CH2:40][CH2:41][CH:42]([CH3:49])[CH2:43][CH2:44][CH2:45][CH:46]([CH3:47])[CH3:48])[CH2:27][CH2:26]2)[O:2][CH2:3][CH2:4][CH:5]([CH2:14][OH:15])[CH2:6][OH:7]

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 21685072HCID 21685072, compound

Product 1

HCID 21685075HCID 21685075, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

27.5 g (0.037 mol) of the 4-(2-tetrahydro-pyranyloxy)-3-(2-tetrahydropyranyloxymethyl)butyl 2,5,7,8-tetramethyl-2-(4',8', 12'-trimethyltridecyl)-6-chromanyl carbonate prepared in the above step was dissolved in 300 ml of methanol. To the obtained solution was added 5 g of p-toluenesulfonic acid followed by stirring at room temperature for 1 hour. 1 l of water was added to the reaction mixture and the oily matter thus separated out was extracted with ether. The extract was washed with water and dried. After distilling off the solvent, the obtained oily residue was purified by column chromatography (silica gel, hexane : ethyl acetate=3:1). Thus 16.5 g of the title compound was obtained as a colorless viscous liquid.

Workup

  1. customthe oily matter thus separated out
  2. extractionwas extracted with ether
  3. washThe extract was washed with water
  4. customdried
  5. distillationAfter distilling off the solvent
  6. customthe obtained oily residue was purified by column chromatography (silica gel, hexane : ethyl acetate=3:1)

Sources & evidence

ORD record
ord-55e0db87119f4492b32d619df623e20a
Source dataset
uspto-grants-1992_04
Patent number
US05102895

Reaction notes

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