Acetyl chloride → Benzyl 4-acetoxypentanoate

HRID 376164Notes

Reaction equation

HRID 376164 reaction equation
[OH:1][CH:2]([CH3:15])[CH2:3][CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].C(N(CC)CC)C.[C:23](Cl)(=[O:25])[CH3:24]>C(Cl)Cl>[C:23]([O:1][CH:2]([CH3:15])[CH2:3][CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:6])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 18991533Benzyl 4-hydroxypentanoate

Product 1

HCID 18991525Benzyl 4-acetoxypentanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

63 g (302.5 mmol) of benzyl 4-hydroxypentanoate and 46.4 ml (332.8 mmol) of triethylamine are charged under nitrogen at room temperature to 300 ml of CH2Cl2. The mixture is cooled to 0° C. and 21.5 ml (302.5 mmol) of acetyl chloride are added dropwise at 0°-5° C. When the dropwise addition is complete, the ice bath is removed and stirring is continued overnight at room temperature. The reaction mixture is mixed with ice-water and the organic phase is separated and washed twice with water. The aqueous phases are extracted twice with CH2Cl2. The organic phases are combined, dried over MgSO4, filtered and concentrated by evaporation. Distillation of the residue gives benzyl 4-acetoxypentanoate as a colourless oil of b.p. 126°-127° C./2.10-2 torr.

Workup

  1. additionWhen the dropwise addition
  2. customthe ice bath is removed
  3. additionThe reaction mixture is mixed with ice-water
  4. customthe organic phase is separated
  5. washwashed twice with water
  6. extractionThe aqueous phases are extracted twice with CH2Cl2
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated by evaporation
  10. distillationDistillation of the residue

Sources & evidence

ORD record
ord-14187e328a334528a365a158b23a0e6f
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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