Sulfuric Acid → 2-Acetoxy-5-chlorobenzonitrile

HRID 369420Notes

Reaction equation

HRID 369420 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[C:11](OC(=O)C)(=[O:13])[CH3:12].S(=O)(=O)(O)O>O>[C:11]([O:10][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=1[C:7]#[N:8])(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 27774205-Chloro-2-hydroxybenzonitrile

Product 1

HCID 106079072-Acetoxy-5-chlorobenzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

5-Chloro-2-hydroxybenzonitrile (39.25 g, 0.25 mol) and acetic anhydride (40 ml) were combined, to which 0.5 ml of concentrated sulfuric acid was added. The reaction mixture was stirred at 60° C. for 10 minutes, followed by the addition of water. Subsequent to extraction with ethyl acetate, the organic layer was washed with 1 N aqueous solution of sodium hydroxide and a saturated aquous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, whereby 45 g of 2-acetoxy-5-chlorobenzonitrile were obtained as a brown solid (yield: 92%). It was provided for immediate use in the next step.

Workup

  1. additionwas added
  2. extractionSubsequent to extraction with ethyl acetate
  3. washthe organic layer was washed with 1 N aqueous solution of sodium hydroxide
  4. dry with materiala saturated aquous solution of sodium chloride, dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-04931d8424e34ecb953a2673b2adb51f
Source dataset
uspto-grants-2000_10
Patent number
US06136848

Reaction notes

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