Hydrochloric Acid → Methyl 2,4-dichloro-alpha-(2,6-dichlorophenyl)benzenepropanoate

HRID 1730172Notes

Reaction equation

HRID 1730172 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[CH2:10][CH:11]([C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:22])[C:12]([OH:14])=[O:13].[CH3:23]O>>[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[CH2:10][CH:11]([C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:22])[C:12]([O:14][CH3:23])=[O:13]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 12391172HCID 12391172, compound

Product 1

HCID 12391182Methyl 2,4-dichloro-alpha-(2,6-dichlorophenyl)benzenepropanoate

Conditions

Temperature
0 °C

Procedure

Gaseous hydrogen chloride is introduced through 200 parts of methanol till saturation, while cooling at 0° C. Then there are added 17 parts of 2,4-dichloro-α-(2,6-dichlorophenyl)benzenepropanoic acid and the whole is stirred and refluxed for 72 hours. The reaction mixture is poured onto water and the product is extracted twice with 1,1'-oxybisethane. The combined extracts are washed successively once with a diluted sodium bicarbonate solution and twice with water, dried, filtered and evaporated. The residue is crystallized from methanol, yielding 13.11 parts of methyl 2,4-dichloro-α-(2,6-dichlorophenyl)benzenepropanoate; mp. 115.1° C.

Workup

  1. temperaturerefluxed for 72 hours
  2. additionThe reaction mixture is poured onto water
  3. extractionthe product is extracted twice with 1,1'-oxybisethane
  4. washThe combined extracts are washed successively once with a diluted sodium bicarbonate solution and twice with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from methanol

Sources & evidence

ORD record
ord-6652fd6989b8458e9555e90811933f08
Source dataset
uspto-grants-1976_11
Patent number
US03991201

Reaction notes

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