Hydrochloric Acid → HCID 20402789, compound

HRID 1702184Notes

Reaction equation

HRID 1702184 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=1[N:12]1[N:16]=[C:15]2[CH:17]=[CH:18][C:19]([CH2:21][CH3:22])=[CH:20][C:14]2=[N:13]1)(=O)C.[OH-].[Na+].Cl>C(O)C>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=1[N:12]1[N:16]=[C:15]2[CH:17]=[CH:18][C:19]([CH2:21][CH3:22])=[CH:20][C:14]2=[N:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20402787HCID 20402787, compound

Product 1

HCID 20402789HCID 20402789, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Pure 2(2-hydroxy-5-methylphenyl)-5-ethyl-2H-benzotriazole was obtained by the hydrolysis of 2(2-acetoxy-5-methylphenyl)5-ethyl-2H-benzotriazole. A solution of 2(2-acetoxy-5-methylphenyl)5-ethyl-2H-benzotriazole (5.9 g, 0.02 mole) and 10 ml of ethanol was poured into a solution of sodium hydroxide (2.0 g, 0.05 mole). The resulting fine dispersion was heated to 80° C. for 3 hours. After cooling to room temperature, the homogeneous solution was acidified with 1 N aqueous hydrochloric acid solution and the solid precipitate was extracted with carbon tetrachloride. The solution was chromatographed and the eluate concentrated under reduced pressure. The residue was recrystallized from n-hexane by cooling the solution to -78° C. White needles were obtained which were collected by filtration, washed with cold n-hexane and dried. 2.7 g (54% yield) of 2(2-hydroxy-5-methylphenyl)5-ethyl-2H-benzotriazole was obtained, which had following properties.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe solid precipitate was extracted with carbon tetrachloride
  3. customThe solution was chromatographed
  4. concentrationthe eluate concentrated under reduced pressure
  5. customThe residue was recrystallized from n-hexane
  6. temperatureby cooling the solution to -78° C
  7. customWhite needles were obtained which
  8. filtrationwere collected by filtration
  9. washwashed with cold n-hexane
  10. customdried

Sources & evidence

ORD record
ord-c85e6ecdee674d218098236adddcb8d0
Source dataset
uspto-grants-1983_04
Patent number
US04380643

Reaction notes

Loading…