Carbon Dioxide → 2-(3,5-Dimethylphenoxy)butanoyl chloride

HRID 1764422Notes

Reaction equation

HRID 1764422 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([CH3:15])[CH:14]=1)[O:5][CH:6]([CH2:10][CH3:11])[C:7](O)=[O:8].C1(C)C=CC=CC=1.C(Cl)([Cl:25])=O.C(=O)=O>O.CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([CH3:15])[CH:14]=1)[O:5][CH:6]([CH2:10][CH3:11])[C:7]([Cl:25])=[O:8]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 1140TolueneHCID 6371PhosgeneHCID 176051682-(3,5-Dimethylphenoxy)butanoic acid

Product 1

HCID 132321262-(3,5-Dimethylphenoxy)butanoyl chlorideYield 101%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(3,5-dimethylphenoxy)-butyric acid [849 g (4.1 moles)], 1075 ml toluene, and 8 ml dimethylformamide was heated to 60° C. in a 5-liter flask fitted with a gas inlet tube, a stirrer, a thermometer and a dry ice condenser. Phosgene, 472 g (4.8 moles), was passed into the solution at 60°-70° C. The mixture was then heated at 60°-70° C. for thirty minutes. The dry ice condenser was then replaced with a water-cooled condenser and the solution was purged with nitrogen to remove excess phosgene and HCl. After 2 hours, purging was discontinued and the solution was vacuum stripped to leave 2-(3,5-dimethylphenoxy)butyryl chloride, 931 g (101% yield), nD30 1.5050.

Workup

  1. customfitted with a gas inlet tube, a stirrer
  2. customwas passed into the solution at 60°-70° C
  3. temperatureThe mixture was then heated at 60°-70° C. for thirty minutes
  4. temperaturecooled condenser
  5. customthe solution was purged with nitrogen
  6. customto remove excess phosgene and HCl
  7. custompurging

Sources & evidence

ORD record
ord-15d08a47bf134f52a92b1652ae5341fd
Source dataset
uspto-grants-1978_09
Patent number
US04116677

Reaction notes

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