4-Chlorobutyryl chloride → HCID 57245589, compound

HRID 1836767Notes

Reaction equation

HRID 1836767 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[Al+3].[Cl-].[Cl-].[Cl-].[C:12]1([CH2:18][C:19]([O:21][CH2:22][CH:23]([CH2:28][CH3:29])[CH2:24][CH2:25][CH2:26][CH3:27])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:15]1[CH:16]=[CH:17][C:12]([CH2:18][C:19]([O:21][CH2:22][CH:23]([CH2:28][CH3:29])[CH2:24][CH2:25][CH2:26][CH3:27])=[O:20])=[CH:13][CH:14]=1)=[O:6]

Participants

4

Reactant 3

HCID 783704-Chlorobutyryl chlorideHCID 2217172-Ethylhexyl phenylacetateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 57245589HCID 57245589, compound

Conditions

Temperature
35 °C

Procedure

Mix chlorobutyryl chloride (16.9 g) and AlCl3 (29.3 g) at room temperature. Add 2-phenylacetic acid, 2-ethylhexyl ester (27.6 g), keeping the temperature below 10° C. Heat at 35° C. for 24 hours, quench in ice water (200 g). Separate the organic phase, dry (MgSO4) and evaporate the solvent in vacuo. Dilute the residue with ethanol (150 mL), add hydrogen chloride, (5 g) and heat to 75° C. After 2.5 hours, add another 5 g of hydrogen chloride and stir at 75° C. for 24 hours. Evaporate the solvent in vacuo to give the title compound.

Workup

  1. customthe temperature below 10° C
  2. customquench in ice water (200 g)
  3. customSeparate the organic phase
  4. dry with materialdry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. additionDilute the residue with ethanol (150 mL)
  7. additionadd hydrogen chloride, (5 g)
  8. temperatureheat to 75° C
  9. additionadd another 5 g of hydrogen chloride
  10. customEvaporate the solvent in vacuo

Sources & evidence

ORD record
ord-2574df1ae65c4f5d8a6d60d4cc8a1a36
Source dataset
uspto-grants-2004_08
Patent number
US06777555B2

Reaction notes

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