Diphenyl carbonate → HCID 86747471, compound

HRID 1197680Notes

Reaction equation

HRID 1197680 reaction equation
[C:1](=[O:16])([O:9]C1C=CC=CC=1)[O:2]C1C=CC=CC=1.[C:17](=[N:25][OH:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:18]>C1(C)C=CC=CC=1>[C:1](=[O:2])([OH:16])[OH:9].[C:17](=[N:25][OH:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:18]

Participants

4

Reactant 2

HCID 7597Diphenyl carbonateHCID 69185Acetophenonoxime

Product 1

HCID 86747471HCID 86747471, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of diphenyl carbonate (5.35g/0.025 mole) and acetophenone oxime (13.5g/0.1 mole) in 25 ml toluene was placed in a 250 ml 3-neck flask fitted with a thermometer and reflux condenser. The mixture was heated to about 116° C. for one (1) hour under nitrogen. Toluene and all low-boiling components were removed under vacuum (70°-75° C. at 2 mm Hg). The syrup gave a solid upon standing. The solid was filtered and washed with 15 ml petroleum ether. The crude product was then dissolved in 20 ml ether and hexane was added to turbidity. After filtering and drying 7.2 g of colorless crystals appeared (m.p. 110°-112° C.). Yield: 97.3%. Confirmation of the compound as acetophenone oxime carbonate was obtained through IR and NMR spectral analyses.

Workup

  1. customfitted with a thermometer
  2. temperaturereflux condenser
  3. customToluene and all low-boiling components were removed under vacuum (70°-75° C. at 2 mm Hg)
  4. customThe syrup gave a solid
  5. filtrationThe solid was filtered
  6. washwashed with 15 ml petroleum ether
  7. dissolutionThe crude product was then dissolved in 20 ml ether
  8. additionhexane was added to turbidity
  9. filtrationAfter filtering
  10. dry with materialdrying 7.2 g of colorless crystals

Sources & evidence

ORD record
ord-9eac2941818d4dea938a4ba586d16b73
Source dataset
uspto-grants-1994_01
Patent number
US05276187

Reaction notes

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