Benzene → HCID 13239466, compound

HRID 371557Notes

Reaction equation

HRID 371557 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([Cl:15])[CH:14]=1)[O:5][CH:6]([CH2:10][CH3:11])[C:7](O)=[O:8].C1C=CC=CC=1.C(Cl)([Cl:24])=O.Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([Cl:15])[CH:14]=1)[O:5][CH:6]([CH2:10][CH3:11])[C:7]([Cl:24])=[O:8]

Participants

6

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric Acid2×HCID 6371Phosgene2×HCID 130607432-(3,5-Dichlorophenoxy)butanoic acid

Product 1

HCID 13239466HCID 13239466, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
35 °C

Procedure

71.8 g. (0.288 moles) of α-(3,5-dichlorophenoxy) butyric acid and 75 ml. of benzene are placed in a 500 ml. flask to which a dropping funnel with dry-ice condenser is attached. The slurry is stirred and the 0.2 ml. dimethyl formamide is added. The mixture is heated to 35° C. and 10 g. of phosgene is condensed into the mixture to initiate reaction. The start of the reaction is evidenced by HCl evolution and foaming. 26.0 g. more phosgene is added in 5 gm. increments. At the conclusion of the reaction (HCl evolution ceasing), the reaction mixture is evaporated leaving a residual liquid α-(3,5-dichlorophenoxy) butyryl chloride 77.6g., ND20 = 1.5345.

Workup

  1. customflask to which a dropping funnel with dry-ice condenser is attached
  2. customcondensed into the mixture
  3. customreaction
  4. customthe reaction mixture is evaporated

Sources & evidence

ORD record
ord-9476c1e8975c4ff3ad5fdf6a777945c9
Source dataset
uspto-grants-1978_05
Patent number
US04087277

Reaction notes

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