Hydrochloric Acid → HCID 13391436, compound

HRID 1731621Notes

Reaction equation

HRID 1731621 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([Cl:27])[C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:16]=[CH:17][CH:18]=1)[O:8][CH:9]([CH3:15])[C:10]([O:12]CC)=[O:11].[OH-].[Na+].Cl>C(O)C.O>[Cl:1][C:2]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([Cl:27])[C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:16]=[CH:17][CH:18]=1)[O:8][CH:9]([CH3:15])[C:10]([OH:12])=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13371122HCID 13371122, compound

Product 1

HCID 13391436HCID 13391436, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 51.4 g (0.124 mol) of the R enantiomer of ethyl 2-[3-(2,6-dichloro-4-trifluoromethyl-phenoxy)phenoxy]-propionate in 95 ml of ethanol was added dropwise to a stirred solution of 5.9 g (0.148 mol) of sodium hydroxide in 145 ml of water at 0° C. During this procedure, the reaction mixture foamed to such an extent that, after 2/3 of the ester solution had been added, a further 10 ml of ethanol had first to be introduced into the reaction mixture before the remainder of the ester solution could be added. Stirring was continued for a further 16 hours, while cooling with ice, and working-up was then carried out by acidifying the mixture with hydrochloric acid, extracting the resulting mixture three times with methylene chloride, drying the extracts and evaporating them down. The remaining residue was boiled with petroleum ether, and the hot mixture was filtered under suction. In this manner, 47.6 g (97.1% of theory) of the R enantiomer of 2-[3-(2,6-dichloro-4-trifluoromethyl-phenoxy)-phenoxy]-propionic acid were obtained in the form of a solid substance of melting point 120° C.

Workup

  1. additionhad been added
  2. additioncould be added
  3. temperaturewhile cooling with ice
  4. extractionextracting the resulting mixture three times with methylene chloride
  5. customdrying the extracts
  6. customevaporating them down
  7. filtrationthe hot mixture was filtered under suction

Sources & evidence

ORD record
ord-4d07d7ffdbd94d21b58d9d7a37476ed1
Source dataset
uspto-grants-1986_11
Patent number
US04622415

Reaction notes

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