Acetyl chloride → HCID 20298532, compound

HRID 1389148Notes

Reaction equation

HRID 1389148 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[C:4]([CH2:14][CH2:15][CH:16]([OH:18])[CH3:17])[CH:3]=1.[C:19](Cl)(=[O:21])[CH3:20]>N1C=CC=CC=1>[C:19]([O:18][CH:16]([CH2:15][CH2:14][C:4]1[CH:3]=[C:2]([F:1])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=1)[CH3:17])(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 10131142HCID 10131142, compound

Product 1

HCID 20298532HCID 20298532, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-(4-Fluoro-6-methoxy-2-naphthyl)-butan-2-ol (2.8 g) was dissolved in pyridine (22 ml) and cooled in an ice-bath. Acetyl chloride (2.9 ml) was added dropwise with stirring. The solution was then stirred for 30 minutes at 0° and 1 hour at room temperature. The suspension produced was poured into ice-water (250 ml) and the product was extracted into ether. The ether was washed with dilute hydrochloric acid and sodium hydrogen carbonate solution. After drying over anhydrous sodium sulphate and solvent was removed under reduced pressure to give the title compound as a pale yellow oil (2.8 g., 85%).

Workup

  1. temperaturecooled in an ice-bath
  2. stirringThe solution was then stirred for 30 minutes at 0° and 1 hour at room temperature
  3. customThe suspension produced
  4. extractionthe product was extracted into ether
  5. washThe ether was washed with dilute hydrochloric acid and sodium hydrogen carbonate solution
  6. dry with materialAfter drying over anhydrous sodium sulphate and solvent
  7. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-6da7b52cd5c2409cb355d62795341481
Source dataset
uspto-grants-1981_01
Patent number
US04243682

Reaction notes

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