Water → Trifop-methyl

HRID 1414113Notes

Reaction equation

HRID 1414113 reaction equation
S(OC)(O[CH3:5])(=O)=O.[F:8][C:9]([F:30])([F:29])[C:10]1[CH:28]=[CH:27][C:13]([O:14][C:15]2[CH:26]=[CH:25][C:18]([O:19][CH:20]([CH3:24])[C:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[CH:12][CH:11]=1.[Na+].O.OP(O)(O)=O>C1(C)C(C)=CC=CC=1>[CH3:5][O:22][C:21](=[O:23])[CH:20]([O:19][C:18]1[CH:25]=[CH:26][C:15]([O:14][C:13]2[CH:12]=[CH:11][C:10]([C:9]([F:29])([F:30])[F:8])=[CH:28][CH:27]=2)=[CH:16][CH:17]=1)[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 1004Phosphoric AcidHCID 6497Dimethyl SulfateHCID 23675546Sodium alpha-[4-(4-Trifluoromethylphenoxy)phenoxy]propionate

Product 1

HCID 94586Trifop-methyl

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
85 °C

Procedure

63 g of dimethyl sulfate are added within 5 minutes and at 130° C. to 348 g of anhydrous sodium-2-[4'-(4"-trifluoromethyl-phenoxy)-phenoxy]-propionate, suspended in 1,000 ml of xylene. After the addition, stirring of the mixture is continued for 1 hour, the mixture is cooled at 85° C., at said temperature 200 ml of water and 0.5 ml of H3PO4 are added and, for the separation of the inorganic salts, the mixture is stirred for 10 minutes. After separation of the water phase, the xylene is distilled off. 340 g of methyl-2-[4'-(4"-trifluoromethyl-phenoxy)-phenoxy]-propionate are obtained melting at 142° C. under 0.05 torr. According to gas chromatogram the content of pure final product is 99.4%, the residual content of unreacted acid is 0.6%, which corresponds to a yield of 99.4%.

Workup

  1. additionAfter the addition
  2. additionare added and, for the separation of the inorganic salts
  3. stirringthe mixture is stirred for 10 minutes
  4. customAfter separation of the water phase
  5. distillationthe xylene is distilled off

Sources & evidence

ORD record
ord-4c4ffb351c7643d1bc21a5c46786903b
Source dataset
uspto-grants-1981_02
Patent number
US04252980

Reaction notes

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