Acetyl chloride → HCID 22457549, compound

HRID 2184711Notes

Reaction equation

HRID 2184711 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][OH:14].C(N(CC)CC)C.[C:22](Cl)(=[O:24])[CH3:23]>C(Cl)Cl>[C:22]([O:14][CH2:13][CH2:12][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]=1[Br:1])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 144921552-(1-Bromonaphthalen-2-yl)ethan-1-ol

Product 1

HCID 22457549HCID 22457549, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-bromo-2-(2-hydroxy-ethyl)-naphthalene (46.5 g, 0.185 mol) in methylene chloride (370 mL) was placed under a nitrogen atmosphere, cooled in an ice bath, and stirred. Triethylamine (32.3 mL, 0.232 mol) was added followed by acetyl chloride (15.8 mL, 0.222 mol) dropwise over 5 minutes. The reaction mixture was removed from the ice bath and stirred at room temperature for 15 minutes. The reaction mixture was washed with water (300 mL), 1N hydrochloric acid (200 mL) and water (250 mL), dried over magnesium sulfate, filtered, and evaporated under vacuum to afford the title compound as an oil (55.1 g).

Workup

  1. temperaturecooled in an ice bath
  2. customThe reaction mixture was removed from the ice bath
  3. stirringstirred at room temperature for 15 minutes
  4. washThe reaction mixture was washed with water (300 mL), 1N hydrochloric acid (200 mL) and water (250 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-0108062794144d43ac809cf42a5fd203
Source dataset
uspto-grants-2002_06
Patent number
US06399597B1

Reaction notes

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