Methanethiol → 4-[4-(2-Chloro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoic acid

HRID 638485Notes

Reaction equation

HRID 638485 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:20]=[CH:19][C:8]([O:9][CH:10]([CH3:18])[C:11]([O:16][CH3:17])=[CH:12][C:13](Cl)=[O:14])=[CH:7][CH:6]=1.CS.N1C=CC=CC=1.CC[O:39]CC>O>[Cl:1][C:2]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:20]=[CH:19][C:8]([O:9][CH:10]([CH3:18])[C:11]([O:16][CH3:17])=[CH:12][C:13]([OH:39])=[O:14])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 878MethanethiolHCID 1049PyridineHCID 3283Diethyl Ether2×HCID 570969654-[4-(2-Chloro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoyl chloride

Product 1

HCID 538603484-[4-(2-Chloro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-[4-(2-chloro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoyl chloride (10 mm.) and ether (10 ml.) is added methyl mercaptan (12 mm.) and pyridine (1 ml.) at about -20°. The mixture is stirred for about 30 minutes and then allowed to rise to about 0° and stand for about 2 hours. The mixture is then diluted with ether and water and the ether phase separated, washed, dried and solvent removed to give the methythiol ester of 4-[4-(2-chloro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoic acid.

Workup

  1. customto rise to about 0°
  2. waitstand for about 2 hours
  3. customthe ether phase separated
  4. washwashed
  5. customdried
  6. customsolvent removed

Sources & evidence

ORD record
ord-ecc5775342a94d00923a9800814f4aa9
Source dataset
uspto-grants-1985_12
Patent number
US04561882

Reaction notes

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