Phosgene → 2-Hydroxybenzonitrile

HRID 1683424Notes

Reaction equation

HRID 1683424 reaction equation
ClCCl.C(=O)=O.[CH:7](=[N:15]O)[C:8]1[C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[OH:10].C(Cl)(Cl)=O>C1(C)C=CC=CC=1>[C:7]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[OH:10])#[N:15]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 7200Salicylaldehyde oximeHCID 21247280dichloromethane Drikold

Product 1

HCID 119072-HydroxybenzonitrileYield 92.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Into a dry 250 ml multi-necked flask equipped with gas tight stirrer, thermometer, pressure equalising dropping funnel and a dichloromethane/Drikold cooled reflux condenser (connected to an aqueous caustic scrubber) were charged salicylaldoxime prepared as described in Example 4 (15.82 g) and toluene (100 ml) to afford a solution which was heated to 93°-95° C. and stirred at this temperature for 0.5 hour. A solution of phosgene in toluene (89.1 g of 20% ww soln.) was then added dropwise, via a dropping funnel, over 0.75 hour whilst maintaining the temperature at 93°-95° C. to afford a pale yellow suspension. The temperature was maintained for 2 hours, after which G.C. analysis indicated reaction was complete. The apparatus was carefully set for atmospheric distillation (ensuring that the equipment was still connected to the caustic scrubber) and the toluene was distilled off up to an internal temperature of 120° C. to give 2-cyanophenol in 92.5% yield based on the phenol used in Example 4.

Workup

  1. customInto a dry 250 ml multi-necked flask equipped with gas tight stirrer
  2. temperaturereflux condenser (
  3. customprepared
  4. customto afford a solution which
  5. temperaturewas heated to 93°-95° C.
  6. addition) was then added dropwise, via a dropping funnel, over 0.75 hour
  7. temperaturewhilst maintaining the temperature at 93°-95° C.
  8. customto afford a pale yellow suspension
  9. temperatureThe temperature was maintained for 2 hours
  10. customreaction
  11. distillationThe apparatus was carefully set for atmospheric distillation (
  12. distillationwas distilled off up to an internal temperature of 120° C.

Sources & evidence

ORD record
ord-1aa5b0a596484970bf42820cd1832ada
Source dataset
uspto-grants-1997_06
Patent number
US05637750

Reaction notes

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