Metaperiodic acid → 3-Chloro-4-cyclohexylbenzaldehyde

HRID 26561

Reaction equation

HRID 26561 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]([OH:17])CO)[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.I(O)(=O)(=O)=O>O1CCCC1.CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1)[CH:14]=[O:17]

Participants

5

Reactant 2

HCID 65185Metaperiodic acidHCID 129398511-(3-Chloro-4-cyclohexylphenyl)ethane-1,2-diol

Product 1

HCID 107277773-Chloro-4-cyclohexylbenzaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 115 g. of 1-(3-chloro-4-cyclohexylphenyl)-1,2-ethanediol in tetrahydrofuran (800 ml.) is added a solution of periodic acid (102 g.) in ether (750 ml.). The reaction mixture is stirred under nitrogen overnight. The reaction mixture is filtered and the filtrate is washed with water (3×200 ml) and placed over sodium sulfate. Removal of solvent gives a liquid residue which is then distilled to give 3-chloro-4-cyclohexylbenzaldehyde.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe filtrate is washed with water (3×200 ml)
  3. customRemoval of solvent
  4. customgives a liquid residue which
  5. distillationis then distilled

Sources & evidence

ORD record
ord-a183d513e694444e977da4dfb50779fe
Source dataset
uspto-grants-1979_04
Patent number
US04150148

Linked notes

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