Metaperiodic acid → 3-Chloro-4-cyclohexylbenzaldehyde

HRID 848610Notes

Reaction equation

HRID 848610 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-9eeadf9004e44932accd2dc2df8f530e
Source dataset
uspto-grants-1981_10
Patent number
US04296264

Reaction notes

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