Benzene → HCID 22290015, compound

HRID 2049948Notes

Reaction equation

HRID 2049948 reaction equation
[C:1]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C1C=CC=CC=1.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(N(CC)CC)C>[C:23]([O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 7412Benzoyl chlorideHCID 123377Phenol, o-(alpha,alpha-dimethylbenzyl)-

Product 1

HCID 22290015HCID 22290015, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Cumylphenyl benzoate is prepared in accordance with the following procedure: one mole of cumylphenol was dissolved in 600 ml of benzene containing 1.2 moles of triethylamine in a 2-liter stirred glass reactor equipped with external heating and cooling devices. The reaction mass was cooled to and maintained at 15°-20° C. during the addition of 1.1 moles of benzoyl chloride over a period of 1.5 hours. After completion of addition, the resulting slurry was heated to and maintained at 40°-45° C. for 1 hour, and thereafter cooled to ambient temperature and filtered. The filter cake was washed with 200 ml of toluene and the combined washings and filtrate distilled to give 214.9 g (68 mole %) of a pale yellow oil having a boiling point at 0.5 mm Hg of 261°-265° C., a specific gravity at 55° C. of 1.082, and a viscosity at 55° C. of 215 cps. On standing, the oil solidified to form a white solid having a melting point of 43°-46.5° C.

Workup

  1. customequipped
  2. temperaturewith external heating
  3. temperaturecooling devices
  4. temperatureThe reaction mass was cooled to and
  5. additionAfter completion of addition
  6. temperaturethe resulting slurry was heated to and
  7. temperaturemaintained at 40°-45° C. for 1 hour
  8. filtrationfiltered
  9. washThe filter cake was washed with 200 ml of toluene
  10. distillationthe combined washings and filtrate distilled
  11. customto give 214.9 g (68 mole %) of a pale yellow oil
  12. customat 0.5 mm Hg of 261°-265° C.
  13. customat 55° C.
  14. customat 55° C.
  15. customto form a white solid

Sources & evidence

ORD record
ord-24bcd67e088847c3b783e69e98c16ff1
Source dataset
uspto-grants-1980_04
Patent number
US04199517

Reaction notes

Loading…