1-Naphthol → HCID 23468261, compound

HRID 443607Notes

Reaction equation

HRID 443607 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CN1CCCC1.[Cl:18][CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1>C1C=CC=CC=1>[C:1]1([O:11][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][C:20]([CH2:19][Cl:18])=[CH:21][CH:22]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 70051-NaphtholHCID 84541-MethylpyrrolidineHCID 701364-(Chloromethyl)benzoyl chloride

Product 1

HCID 23468261HCID 23468261, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

72.1 g (0.5 mole) of α-naphthol was heated to 50° C. with 150 ml of benzene and 0.5 ml of N-methylpyrrolidine, whereupon a clear solution was obtained. Following the procedure of Method C, 95 g (0.5 mole) of p-chloromethylbenzoyl chloride dissolved in 80 ml of benzene was added drop by drop over a period of about 30 minutes, and then the mixture was refluxed for 5 hours under a weak current of nitrogen gas. The benzene was then distilled from the clear, orange-colored solution. The residue crystallized upon cooling to a yellow mass amounting to 148 g (100%), M.P. 93°-96° C. The entire amount of the raw product was recrystallized from 3 liters of cyclohexane with the addition of decolorizing carbon. About 80% of the material put in was obtained in light yellow needles of a melting point of 104°-106° C. For the analysis, 20 g was again recrystallized from 400 ml of cyclohexane. 16.5 g of very pale yellow needles was obtained, M.P. 105°-106.5° C.

Workup

  1. customwas obtained
  2. additionwas added drop by drop over a period of about 30 minutes
  3. temperaturethe mixture was refluxed for 5 hours under a weak current of nitrogen gas
  4. distillationThe benzene was then distilled from the clear, orange-colored solution
  5. customThe residue crystallized
  6. temperatureupon cooling to a yellow mass amounting to 148 g (100%), M.P. 93°-96° C
  7. customThe entire amount of the raw product was recrystallized from 3 liters of cyclohexane with the addition of decolorizing carbon
  8. customin was obtained in light yellow needles of a melting point of 104°-106° C
  9. customFor the analysis, 20 g was again recrystallized from 400 ml of cyclohexane
  10. custom16.5 g of very pale yellow needles was obtained

Sources & evidence

ORD record
ord-a0e95091ba6543f48cc46c43eb74a89f
Source dataset
uspto-grants-1981_04
Patent number
US04260803

Reaction notes

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