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

HRID 494939Notes

Reaction equation

HRID 494939 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 93.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

145 mg of 8-(2,3-dihydroxypropyl)-7-methoxy-2,2-dimethyl-4-oxochroman was dissolved in 3 ml of tetrahydrofuran and 4 ml of methanol. Thereafter, 7 ml of water containing 0.22 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 filtered. The organic layer was then concentrated under a reduced pressure, so as to obtain 120 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. filtrationfiltered
  5. concentrationThe organic layer was then concentrated under a reduced pressure

Sources & evidence

ORD record
ord-bbd3cc20e26a469f8b1f4fb4cad835d6
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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