Diethyl Ether → (1,1'-Biphenyl)-4-carboxaldehyde

HRID 840170Notes

Reaction equation

HRID 840170 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.C(C1C=C[NH+]=CC=1)C1C=CC=CC=1.C(C1C=C[NH+]=CC=1)C1C=CC=CC=1.[C:36]1([C:42]2[CH:49]=[CH:48][C:45]([CH2:46][OH:47])=[CH:44][CH:43]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(OCC)C.CCCCCC>ClCCl>[C:36]1([C:42]2[CH:43]=[CH:44][C:45]([CH:46]=[O:47])=[CH:48][CH:49]=2)[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8058HexaneHCID 19186(1,1'-Biphenyl)-4-methanolHCID 14900616HCID 14900616, compound

Product 1

HCID 76689(1,1'-Biphenyl)-4-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

65 mmol of 4-benzylpyridinium dichromate are added to 54 mmol of 4-phenylbenzyl alcohol in 400 ml of dichloromethane. The reaction mixture is stirred for 2 hours at room temperature. 600 ml of a mixture of ethyl ether and hexane in a ratio of 1 to 1 are added. After stirring for 30 minutes, the mixture is filtered. The filtrate is washed once with 100 ml of a 1N hydrochloric acid solution. The organic phase is dried over magnesium sulphate and then concentrated to yield the expected compound.

Workup

  1. stirringAfter stirring for 30 minutes
  2. filtrationthe mixture is filtered
  3. washThe filtrate is washed once with 100 ml of a 1N hydrochloric acid solution
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c99d272e0ca94d708f33eb8afd34a71f
Source dataset
uspto-grants-2002_04
Patent number
US06365605B1

Reaction notes

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