Oxalyl chloride → Hexanoylacetyl Chloride

HRID 1032623Notes

Reaction equation

HRID 1032623 reaction equation
[C:1]([CH2:8][C:9]([OH:11])=O)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(Cl)(=O)C([Cl:15])=O>CCCCCC>[C:1]([CH2:8][C:9]([Cl:15])=[O:11])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 1288593-Ketooctanoic acid

Product 1

HCID 22164584Hexanoylacetyl ChlorideYield 98%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
55 °C

Procedure

8.7g (0.05 m) of hexanoylacetic acid and 12.7 g (0.10m) of oxalyl chloride were mixed together at room temperature. The reaction was heated gradually over one hour to 50-60° C., then to 60-70° C. under aspirator pressure for one hour. The reaction mixture was diluted with 125 ml hexane, washed with 3×100 ml ice water, dried over 20 g MgSO4, and roto-vapped at 50° C. to yield an oil (9.4 g, 98% yield).

Workup

  1. washwashed with 3×100 ml ice water
  2. dry with materialdried over 20 g MgSO4

Sources & evidence

ORD record
ord-f307a8a06b3e4b2da1a6b166a85da23c
Source dataset
uspto-grants-1990_09
Patent number
US04959187

Reaction notes

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