Benzoyl chloride → Dibenzoyl selenide

HRID 1730834Notes

Reaction equation

HRID 1730834 reaction equation
[Se-2:1].[Na+].[Na+].[Se].[BH4-].[Na+].[SeH2].[Na].[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:18](=[O:21])(O)[O-].[Na+]>O>[C:9]([Se:1][C:18](=[O:21])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 6

HCID 7412Benzoyl chlorideHCID 73973Sodium selenideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 6326970SeleniumHCID 131710529CID 131710529

Product 1

HCID 11536582Dibenzoyl selenide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A sodium selenide solution is initially prepared by the reaction of about 3.2 grams (0.04 moles) of selenium powder with about 3 grams (0.08 moles) sodium borohydride in water according to the method described by D. L. Klayman et al, J. Am. Chem. Soc. 95, 197 (1973). The flask containing the sodium hydrogen selenide solution is purged of air with nitrogen and about 11.2 grams (0.08 moles) benzoyl chloride and about 10 grams sodium bicarbonate added to the reaction mixture with mild agitation. The ingredients within the flask are allowed to react at room temperature under nitrogen for 14 hours. The solid products are separated from the reaction medium by filtration, washed with water and recrystallized from a benzene/hexane solution to yield colorless needle like crystals, (m.p. 60°- 61° C).

Workup

  1. additionadded to the reaction mixture with mild agitation
  2. customto react at room temperature under nitrogen for 14 hours
  3. customThe solid products are separated from the reaction medium by filtration
  4. washwashed with water
  5. customrecrystallized from a benzene/hexane solution
  6. customto yield colorless needle like crystals, (m.p. 60°- 61° C)

Sources & evidence

ORD record
ord-e51e9365212c4edeb91884889ad2bfbc
Source dataset
uspto-grants-1976_11
Patent number
US03994791

Reaction notes

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