Water → p-Toluic acid, 3,5-dimethylphenyl ester

HRID 1395053Notes

Reaction equation

HRID 1395053 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([C:7](Cl)=[O:8])=[CH:3][CH:2]=1.[CH3:11][C:12]1[CH:13]=[C:14]([OH:19])[CH:15]=[C:16]([CH3:18])[CH:17]=1.C(OCC)C.O>N1C=CC=CC=1>[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([C:7]([O:19][C:14]2[CH:15]=[C:16]([CH3:18])[CH:17]=[C:12]([CH3:11])[CH:13]=2)=[O:8])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 79483,5-DimethylphenolHCID 134054-Methylbenzoyl Chloride

Product 1

HCID 532505p-Toluic acid, 3,5-dimethylphenyl esterYield 84.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

p-Toluoyl chloride (154 g.) was added during 30 minutes to a solution of 3,5-dimethylphenol (122 g.) in anhydrous pyridine (200 ml.), with stirring. The temperature rose to 80° C. The mixture was stirred and heated on the steambath for 3 hours, and was then cooled and stirred with diethyl ether (500 ml.) and water (2000 ml.). The organic layer was separated, and the aqueous layer was further extracted with diethyl ether (3×250 ml.). The combined ether solutions were washed with N aqueous sodium hydroxide solution to remove unchanged starting materials and with 2 N hydrochloric acid to remove pyridine, and finally with water. The solution was dried over anhydrous sodium sulphate and evaporated in vacuo, and the residue was recrystallised from light petroleum (b.p. 40°-60° C.; 550 ml.) to give 3.5-dimethylphenyl p-toluate (203 g.). m.p. 55°-57° C.

Workup

  1. customrose to 80° C
  2. stirringThe mixture was stirred
  3. temperatureheated on the steambath for 3 hours
  4. temperaturewas then cooled
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was further extracted with diethyl ether (3×250 ml.)
  7. washThe combined ether solutions were washed with N aqueous sodium hydroxide solution
  8. customto remove unchanged
  9. customwith 2 N hydrochloric acid to remove pyridine
  10. dry with materialThe solution was dried over anhydrous sodium sulphate
  11. customevaporated in vacuo
  12. customthe residue was recrystallised from light petroleum (b.p. 40°-60° C.; 550 ml.)

Sources & evidence

ORD record
ord-260af01780cf406a91b844628310e040
Source dataset
uspto-grants-1980_05
Patent number
US04201790

Reaction notes

Loading…