Methanol → HCID 70614365, compound

HRID 866623Notes

Reaction equation

HRID 866623 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:7]=1.[CH3:20]O.S(=O)(=O)(O)O>O>[CH3:20][O:10][C:9](=[O:11])[CH2:8][C:6]1[CH:7]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=1[S:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 70614197HCID 70614197, compound

Product 1

HCID 70614365HCID 70614365, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

47 g. of crude 5-methyl-2-(4-methylthio-phenoxy)-phenylacetic acid are dissolved in 170 ml. of methanol. 19 Ml. of concentrated sulfuric acid are added dropwise with stirring and the mixture is subsequently heated at reflux for 3.5 hours. After cooling, the mixture is diluted with water and extracted several times with benzene. The benzene extracts are washed with water, sodium bicarbonate solution and again with water. After evaporation of the solvent, there remains a residue which is chromatographed on 400 g. of silica gel. By elution with benzene, there is obtained 5-methyl-2-(4-methylthio-phenoxy)-phenylacetic acid methyl ester, which ester is dissolved in 73 ml. of methanol, treated with 18.8 g. of potassium hydroxide and 73 ml. of water and subsequently heated at reflux for 1 hour. Thereafter, the methanol is removed in vacuo and the residue acidified with hydrochloric acid. The mixture is extracted with benzene, the benzene extract washed with water and concentrated in vacuo. The residue is crystallized from cyclohexane, and there is obtained 5-methyl-2-(4-methylthio-phenoxy)-phenylacetic acid having a melting point of 81°-83° C.

Workup

  1. temperaturethe mixture is subsequently heated
  2. temperatureat reflux for 3.5 hours
  3. temperatureAfter cooling
  4. extractionextracted several times with benzene
  5. washThe benzene extracts are washed with water, sodium bicarbonate solution and again with water
  6. customAfter evaporation of the solvent, there
  7. customis chromatographed on 400 g
  8. washBy elution with benzene

Sources & evidence

ORD record
ord-f665078ea87e4290bef8ca6873958913
Source dataset
uspto-grants-1978_07
Patent number
US04100173

Reaction notes

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