Butyryl chloride → HCID 57088105, compound

HRID 330778Notes

Reaction equation

HRID 330778 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[C:12](Cl)(=[O:16])[CH2:13][CH2:14][CH3:15]>N1C=CC=CC=1.O>[C:12]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:3]=1)(=[O:16])[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 8855Butyryl chlorideHCID 121243-Hydroxyacetanilide

Product 1

HCID 57088105HCID 57088105, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

N-(3-Hydroxyphenyl)acetamide (300 g) was stirred in pyridine (990 mL) followed by the addition of butyryl chloride (246 mL). This reaction was stirred at room temperature for 30 min. The resulting crystalline suspension was left for 18 hrs. to ensure completion. The mixture was dissolved in water and ethyl acetate (1:1, 1000 mL), the organic layer was separated and washed with brine (3×1000 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo at 70° C. to remove pyridine. Upon cooling the oil become a very low melting solid. This solid was carefully added to a coarse 500 mL frit and dried. Minimal washing with ice cold hexane was used to cake the solid. The final compound was collected to provide the title compound in 75% yield (440 g) as a light-yellow solid.

Workup

  1. waitThe resulting crystalline suspension was left for 18 hrs
  2. customethyl acetate (1:1, 1000 mL), the organic layer was separated
  3. washwashed with brine (3×1000 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo at 70° C.
  6. customto remove pyridine
  7. temperatureUpon cooling the oil
  8. additionThis solid was carefully added to a coarse 500 mL frit
  9. customdried
  10. washMinimal washing with ice cold hexane
  11. customThe final compound was collected

Sources & evidence

ORD record
ord-9ef39d0072a04c8fae4a49b2c527a016
Source dataset
uspto-grants-2014_11
Patent number
US08877752B2

Reaction notes

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