Triacetoxyperiodinane → 3-Methoxy-4-methylbenzaldehyde

HRID 1784946Notes

Reaction equation

HRID 1784946 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH2:32][OH:33])[CH:28]=[CH:29][C:30]=1[CH3:31]>C(Cl)Cl.CCOCC>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:28]=[CH:29][C:30]=1[CH3:31])[CH:32]=[O:33]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 11744818(3-methoxy-4-methylphenyl)methanol

Product 1

HCID 47150953-Methoxy-4-methylbenzaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dess-Martin periodinane (3 gm, 7.07 mmol) was added to (3-methoxy-4-methylphenyl)methanol (1 gm, 6.57 mmol) in CH2Cl2 (35 ml) at 0° C. After stirring at 0° C. for 0.5 h, some of the CH2Cl2 was removed, reaction mixture was diluted with ether, washed with sodium bicarbonate solution, sodium thiosulfate solution and water. Organic layer was dried and evaporated to obtain 3-methoxy-4-methylbenzaldehyde in quantitative yield.

Workup

  1. customsome of the CH2Cl2 was removed
  2. customreaction mixture
  3. washwashed with sodium bicarbonate solution, sodium thiosulfate solution and water
  4. customOrganic layer was dried
  5. customevaporated

Sources & evidence

ORD record
ord-ab97beeb08ef422c827061ccca03d900
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Reaction notes

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