Dichloromethane → HCID 86756213, compound

HRID 565159Notes

Reaction equation

HRID 565159 reaction equation
[C:1]1([CH3:23])[CH:6]=[CH:5][C:4]([C:7]#[C:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH2:20][CH2:19][CH:18]([CH2:21][OH:22])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.ClCCl.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(O)(C)C>[C:1]1([CH3:23])[CH:2]=[CH:3][C:4]([C:7]#[C:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH2:20][CH2:19][CH:18]([CH:21]=[O:22])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70220377HCID 70220377, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86756213HCID 86756213, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

36.6 g of [4-(4-p-tolylethynylphenyl)cyclohexyl]methanol were mixed with 300 ml of dichloromethane, and a mixture of 21 g of Celite and 28.5 g of pyridinium chlorochromate (PCC) were added under a nitrogen atmosphere. The reaction mixture was stirred overnight at RT. 100 ml of isopropanol were then added to the black suspension, and the mixture was stirred at RT for 1½ hours in order to destroy the excess PCC. This suspension was then filtered, and the filtrate was subjected to conventional work-up, giving 4-(4-p-tolylethynylphenyl)cyclohexanecarbaldehyde in the form of a colorless solid.

Workup

  1. additionwere added under a nitrogen atmosphere
  2. stirringthe mixture was stirred at RT for 1½ hours in order
  3. customto destroy the excess PCC
  4. filtrationThis suspension was then filtered

Sources & evidence

ORD record
ord-155d8f6b8fc1447bb89faeea97d3f6ee
Source dataset
uspto-grants-2001_01
Patent number
US06171664B2

Reaction notes

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