Toluene → (R)-2-(2,4-Dichlorophenoxy)propionyl chloride

HRID 1586276Notes

Reaction equation

HRID 1586276 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:3]=1[O:4][C@H:5]([CH3:9])[C:6](O)=[O:7].C1(C)C=CC=CC=1.S(Cl)([Cl:24])=O>CN(C)C=O>[Cl:1][C:2]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:3]=1[O:4][C@H:5]([CH3:9])[C:6]([Cl:24])=[O:7]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 119435Dichlorprop-P

Product 1

HCID 11118592(R)-2-(2,4-Dichlorophenoxy)propionyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A stirred mixture of (R)-2-(2,4-dichlorophenoxy)propionic acid (588 g, 2.5 mol), 588 g of toluene and 0.6 g of dimethyl formamide (DMF) is heated to 75° C., treated with thionyl chloride (304 g, 2.55 mol) over a 1.5 hour period, heated at 75° C. for 1 hour and cooled to 20-25° C. The resultant reaction mixture may be distilled to obtain the title product in quantitative yield, as an amber oil, or used as is in the next process step. The isolated product is characterized by NMR analysis. The product toluene solution is assayed by HPLC analysis.

Workup

  1. temperatureheated at 75° C. for 1 hour
  2. temperaturecooled to 20-25° C
  3. customThe resultant reaction mixture
  4. distillationmay be distilled

Sources & evidence

ORD record
ord-ea4458f7c2cf418280844cc24729398b
Source dataset
uspto-grants-1999_08
Patent number
US05942640

Reaction notes

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