Water → (7-Methoxy-2,2-dimethyl-4-oxochroman-8-yl)acetaldehyde

HRID 494944Notes

Reaction equation

HRID 494944 reaction equation
[OH:1][CH:2](CO)[CH2:3][C:4]1[C:5]([O:17][CH3:18])=[CH:6][CH:7]=[C:8]2[C:13]=1[O:12][C:11]([CH3:15])([CH3:14])[CH2:10][C:9]2=[O:16].O.I([O-])(=O)(=O)=O.[Na+]>O1CCCC1.CO.C(OCC)(=O)C>[CH3:18][O:17][C:5]1[C:4]([CH2:3][CH:2]=[O:1])=[C:13]2[C:8]([C:9](=[O:16])[CH2:10][C:11]([CH3:14])([CH3:15])[O:12]2)=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 576828558-(2,3-Dihydroxypropyl)-7-methoxy-2,2-dimethyl-4-oxochroman

Product 1

HCID 57682772(7-Methoxy-2,2-dimethyl-4-oxochroman-8-yl)acetaldehydeYield 107.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

171 mg of 8-(2,3-dihydroxypropyl)-7-methoxy-2,2-dimethyl-4-oxochroman was dissolved in 4 ml of tetrahydrofuran and 4 ml of methanol. Thereafter, 8 ml of water containing 0.26 g of sodium metaperiodate was added to the reaction solution while cooling on ice, and the obtained mixture was then stirred at room temperature for 30 minutes. The reaction solution was diluted with ethyl acetate and then washed with a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure, so as to obtain 163 mg of (7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)acetaldehyde. This compound was used in the following reaction without further purification.

Workup

  1. temperaturewhile cooling on ice
  2. washwashed with a saturated sodium chloride aqueous solution
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-108d9d96408c417a9a3dc5d69d082193
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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