Acetyl chloride → Nopyl acetate

HRID 1682255Notes

Reaction equation

HRID 1682255 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][C:6]1([CH3:16])[CH:11]2[CH2:12][CH:7]1[CH2:8][CH:9]=[C:10]2[CH2:13][CH2:14][OH:15].C(N(CC)CC)C>ClCCl>[CH3:2][C:1]([O:15][CH2:14][CH2:13][C:10]1[C@H:11]2[C:6]([CH3:16])([CH3:5])[C@H:7]([CH2:12]2)[CH2:8][CH:9]=1)=[O:3]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 31408Nopol

Product 1

HCID 929336Nopyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 g of acetyl chloride (=0.64 mole) were slowly added dropwise to a solution of 100 g of (-)-nopol (=0.6 mole) and 130 ml of triethylamine (=0.93 mole) in 600 ml of dichloromethane while cooling in ice at a temperature of 5° to 10° C. The reaction mixture was subsequently stirred at 5° to 10° C. for a further 20 minutes. The reaction mixture was then further stirred without cooling until it had warmed to room temperature. To work up the reaction mixture, it was stirred into 800 ml of ice-water. The organic phase was separated, the aqueous phase was washed with 100 ml of dichloromethane, and the combined organic phases were washed to neutrality with saturated aqueous sodium bicarbonate solution and dried over sodium sulfate. The residue after removal of the dichloromethane by distillation was 130 g of crude product, from which (-)-nopyl acetate was isolated by fractional distillation. 98 g of (-)-nopyl acetate with a boiling point of 117°-119° C. (10 mm Hg) and a refractive index nD20 =1.4722 were obtained.

Workup

  1. temperaturewhile cooling in ice at a temperature of 5° to 10° C
  2. stirringThe reaction mixture was then further stirred
  3. temperaturewithout cooling until it
  4. customThe organic phase was separated
  5. washthe aqueous phase was washed with 100 ml of dichloromethane
  6. washthe combined organic phases were washed to neutrality with saturated aqueous sodium bicarbonate solution
  7. dry with materialdried over sodium sulfate
  8. customThe residue after removal of the dichloromethane
  9. distillationby distillation

Sources & evidence

ORD record
ord-bb1dfe845500462580e2b7631d5b1a1e
Source dataset
uspto-grants-1992_12
Patent number
US05175347

Reaction notes

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