Selenium Dioxide → 2-(p-Chlorobenzoyl)-benzaldehyde

HRID 328678Notes

Reaction equation

HRID 328678 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH:6]([OH:15])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:13][OH:14])=[CH:4][CH:3]=1.[Se](=O)=O>C(O)(=O)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:13]=[O:14])=[O:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 197815594'-Chloro-2-hydroxymethylbenzhydrol

Product 1

HCID 199363582-(p-Chlorobenzoyl)-benzaldehyde

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 18.6 g. of 4'-chloro-2-hydroxymethylbenzhydrol in 100 ml. of acetic acid and 10.4 g. selenium dioxide was refluxed for 2 hours. The mixture was poured on ice and made alkaline and extracted with ether. Concentration of the ether solution and addition of petroleum ether gave pale yellow prisms which after recrystallization from a mixture of ether and petroleum ether gave 2-(p-chlorobenzoyl)-benzaldehyde melting at 112°-113°. Ultraviolet inflexion (2-propanol) at 225 μ (ε = 17,500) and maximum at 259 μ (ε = 22,500), infrared absorption (CHCL3) at 1670 cm-1 and 1705 cm-1.

Workup

  1. additionThe mixture was poured on ice
  2. extractionextracted with ether
  3. additionConcentration of the ether solution and addition of petroleum ether
  4. customgave pale yellow prisms which
  5. customafter recrystallization
  6. additionfrom a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-709c0c144ae94caaa289b9d403638d13
Source dataset
uspto-grants-1977_04
Patent number
US04018765

Reaction notes

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