Dichloromethane methanol → HCID 16049921, compound

HRID 751450Notes

Reaction equation

HRID 751450 reaction equation
[OH:1][C:2](/[C:5](=[CH:8]/[I:9])/[CH2:6][OH:7])([CH3:4])[CH3:3].C(Cl)Cl.CO>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[OH:1][C:2](/[C:5](=[CH:8]/[I:9])/[CH:6]=[O:7])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 21226129Dichloromethane methanolHCID 58924668HCID 58924668, compound

Product 1

HCID 16049921HCID 16049921, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of E-2-(1-hydroxy-1-methylethyl)-3-iodoprop-2-en-1-ol (III) (5.7 mmol, 1.4 g) in dry methylene chloride (25 ml), manganese dioxide (10 eq., 57 mmol, 5 g) is added in portions, at room temperature (rt), under an inert atmosphere. The progress of the reaction is monitored by analytical chromatography on a silica gel plate (eluent CH2Cl2/MeOH 97/3). After the disappearance of the starting material, the mixture is filtered on Celite®. The filtrate, evaporated under reduced pressure, gives Z-2-(1-hydroxy-1-methylethyl)-3-iodopropenal (IV) (1.3 g, 94%) in the form of a slightly yellow oil.

Workup

  1. filtrationAfter the disappearance of the starting material, the mixture is filtered on Celite®
  2. customThe filtrate, evaporated under reduced pressure

Sources & evidence

ORD record
ord-3b6678daa30445c3954184677ccd9ce2
Source dataset
uspto-grants-2008_07
Patent number
US07405309B2

Reaction notes

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