HCID 21685077, compound → HCID 21685078, compound

HRID 1029987Notes

Reaction equation

HRID 1029987 reaction equation
[C:1](=[O:44])([O:13][C:14]1[C:15]([CH3:43])=[C:16]2[C:21](=[C:22]([CH3:25])[C:23]=1[CH3:24])[O:20][C:19]([CH3:42])([CH2:26][CH2:27][CH2:28][CH:29]([CH3:41])[CH2:30][CH2:31][CH2:32][CH:33]([CH3:40])[CH2:34][CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38])[CH2:18][CH2:17]2)[O:2][CH2:3][C:4]1([CH3:12])[CH2:9][O:8]C(C)(C)[O:6][CH2:5]1>Cl.CO>[C:1](=[O:44])([O:13][C:14]1[C:15]([CH3:43])=[C:16]2[C:21](=[C:22]([CH3:25])[C:23]=1[CH3:24])[O:20][C:19]([CH3:42])([CH2:26][CH2:27][CH2:28][CH:29]([CH3:41])[CH2:30][CH2:31][CH2:32][CH:33]([CH3:40])[CH2:34][CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38])[CH2:18][CH2:17]2)[O:2][CH2:3][C:4]([CH2:5][OH:6])([CH2:9][OH:8])[CH3:12]

Participants

4

Reactant 1

HCID 21685077HCID 21685077, compound

Product 1

HCID 21685078HCID 21685078, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

10 g of 2,2,5-trimethyl-1,3-dioxan-5-ylmethyl 2,5,7,8-tetramethyl-2-(4',8', 12'-trimethyl-tridecyl)-6-chromanyl carbonate was dissolved in a mixture of 70 ml of 2 N hydrochloric acid and 35 ml of methanol and heated under reflux for 4.5 hours. After cooling, the reaction mixture was extracted with 500 ml of ethyl acetate and 400 ml of water. The extract was washed with water, dried and concentrated. Then the obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate). Thus 7.4 g of the title compound was obtained as a colorless and starch syrup-like product.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4.5 hours
  3. temperatureAfter cooling
  4. extractionthe reaction mixture was extracted with 500 ml of ethyl acetate and 400 ml of water
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThen the obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-734067f9266745f79195b3b1332e4a51
Source dataset
uspto-grants-1992_04
Patent number
US05102895

Reaction notes

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