Phenol → HCID 19609280, compound

HRID 443606Notes

Reaction equation

HRID 443606 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:8][CH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](Cl)=[O:13]>C1C=CC=CC=1.N1C=CC=CC=1.C(O)(C)C>[C:1]1([O:7][C:12](=[O:13])[C:11]2[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=2[CH2:9][Cl:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 996PhenolHCID 30163952-(Chloromethyl)benzoyl chloride

Product 1

HCID 19609280HCID 19609280, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 241BenzeneSolventHCID 3776IsopropanolSolvent2×

Conditions

Temperature
-20 °C

Procedure

The ester was prepared by Method C only, by dissolving 47 g (0.5 mole) of phenol in 60 ml of benzene in the apparatus used in the preparation of the para compound, adding 0.5 ml of absolute pyridine as catalyst, and then adding 95 g (0.5 mole) of undiluted o-chloromethylbenzoyl chloride drop by drop at 55° to 60° C. over a period of about 1 hour, the mixture being stirred for another 4 hours at the refluxing temperature to complete the reaction. The benzene was then distilled out of the clear, light red solution thus obtained. The viscous oily, clear, red residue obtained in a quantitative yield crystallized after standing for a while at -15° C. The crystal mass thus obtained was ground in a chilled mortar with about 100 ml of intensely cooled isopropanol; the undissolved portion was removed by suction filtering and washed with 100 ml of isopropanol chilled to -20° C. After drying, 87 g (70%) was obtained of a colorless crystallizate with a melting point of 39°-41° C. For the analysis, 15 g was dissolved at 35° C. in 125 ml of isopropanol and set aside to crystallize at -20° C. 12.7 g of colorless needles was obtained with a melting point of 39°-41° C.

Workup

  1. customused in the preparation of the para compound
  2. customthe reaction
  3. distillationThe benzene was then distilled out of the clear, light red solution
  4. customthus obtained
  5. customThe viscous oily, clear, red residue obtained in a quantitative yield
  6. customcrystallized
  7. customafter standing for a while at -15° C
  8. customThe crystal mass thus obtained
  9. customthe undissolved portion was removed by suction
  10. filtrationfiltering
  11. washwashed with 100 ml of isopropanol
  12. customAfter drying
  13. custom87 g (70%) was obtained of a colorless crystallizate with a melting point of 39°-41° C
  14. customto crystallize at -20° C

Sources & evidence

ORD record
ord-c7d2480ee72c4d2d958c980021dcbc72
Source dataset
uspto-grants-1981_04
Patent number
US04260803

Reaction notes

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