HCID 18521577, compound → HCID 18521566, compound

HRID 413699Notes

Reaction equation

HRID 413699 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([O:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=1[C:16]([CH3:21])([CH3:20])[CH2:17][CH2:18][OH:19])=[O:6].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Br:1][CH2:2][CH2:3][CH2:4][C:5]([O:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=1[C:16]([CH3:21])([CH3:20])[CH2:17][CH:18]=[O:19])=[O:6]

Participants

4

Reactant 2

HCID 18521577HCID 18521577, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 18521566HCID 18521566, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
24 °C

Procedure

2.5 g of 3-[2-(4-bromobutyryloxy)-4,6-dimethylphenyl]-3,3-dimethylpropan-1-ol in solution in 160 cm3 of dichloromethane are added dropwise, at 24° C., to 3.1 g of pyridinium chlorochromate in suspension in 900 cm3 of dichloromethane. After stirring for 2 hours at 24° C., the reaction mixture is filtered on 630 g of silica (particle size 0.063-0.2 mm), eluting successively with pure dichloromethane, and then a mixture of dichloromethane and ethyl acetate (80/20 by volume). 2.4 g of 3-[2-(4-bromobutyryloxy)-4,6-dimethylphenyl]-3,3-dimethylpropanal are thus obtained in the form of a colorless viscous oil.

Workup

  1. filtrationthe reaction mixture is filtered on 630 g of silica (particle size 0.063-0.2 mm)
  2. washeluting successively with pure dichloromethane
  3. additiona mixture of dichloromethane and ethyl acetate (80/20 by volume)

Sources & evidence

ORD record
ord-7a655a5c980545a4a3fb5feb5551dbb5
Source dataset
uspto-grants-2003_05
Patent number
US06569854B1

Reaction notes

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