Methanol → HCID 19853974, compound

HRID 1650404Notes

Reaction equation

HRID 1650404 reaction equation
S(=O)(=O)(O)O.CO.[CH3:8][C:9](=[CH2:18])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15].[CH3:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=1[CH3:26]>O>[CH3:19][C:20]1[CH:21]=[C:22]([C:9]([CH3:18])([CH3:8])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:23]=[CH:24][C:25]=1[CH3:26]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 7237O-XyleneHCID 12590016HCID 12590016, compound

Product 1

HCID 19853974HCID 19853974, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

300 parts of 98% sulfuric acid, 64 parts of methanol, 71 parts of methyl 5-methylhex-5-enecarboxylate and 53 parts of o-xylene are stirred at room temperature for 3 days and then poured into 2000 parts of water. This is followed by extraction with ether, washing of the extract with water and evaporation of the ether. The residue is dissolved in 500 parts of methanol, one part of p-toluenesulfonic acid, and the mixture is heated under reflux for 6 hours. The methanol is then distilled off, and the residue is taken up in ether and washed first with aqueous sodium bicarbonate and then with water. The ether is evaporated off and the residue is distilled to give methyl 5-(3,4-dimethylphenyl)-5-methylhexanecarboxylate having a boiling point of 176°-182° C./16 mbar.

Workup

  1. extractionThis is followed by extraction with ether
  2. washwashing of the
  3. extractionextract with water and evaporation of the ether
  4. dissolutionThe residue is dissolved in 500 parts of methanol, one part of p-toluenesulfonic acid
  5. temperaturethe mixture is heated
  6. temperatureunder reflux for 6 hours
  7. distillationThe methanol is then distilled off
  8. washwashed first with aqueous sodium bicarbonate
  9. customThe ether is evaporated off
  10. distillationthe residue is distilled

Sources & evidence

ORD record
ord-db4c215ad23841709f29350362ea2387
Source dataset
uspto-grants-1990_05
Patent number
US04924015

Reaction notes

Loading…