Hydrochloric Acid → HCID 178466791, compound

HRID 127479Notes

Reaction equation

HRID 127479 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:12][N:11]=[N:10][N:9]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:17](Cl)(=[O:19])[CH3:18].Cl>C(Cl)Cl>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:17](=[O:19])[CH3:18])=[CH:4][C:3]=1[C:8]1[NH:12][N:11]=[N:10][N:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 178515941HCID 178515941, compound

Product 1

HCID 178466791HCID 178466791, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 16.2 g (0.1 mol) of 5-(2-hydroxyphenyl)-1H-tetrazole in 300 ml of dry methylene chloride is cooled in an ice bath, 39.9 g (0.3 mol) of anhydrous aluminum chloride are added and acetyl chloride 8.1 g (0.1 mol) is added via dropwise addition over a period of 5 minutes. The mixture is refluxed for 3.5 hours, cooled, and 200 ml of 2N HCl is added dropwise with stirring. The resulting precipitate is collected, washed with 2N HCl, water and recrystallized from an isopropanol-water mixture to yield 8.0 g of 1-[4-hydroxy-3-(1H-tetrazol-5-yl)phenyl]ethanone, m.pt. 260°-261° C. (dec.).

Workup

  1. temperatureis cooled in an ice bath
  2. temperatureThe mixture is refluxed for 3.5 hours
  3. temperaturecooled
  4. customThe resulting precipitate is collected
  5. washwashed with 2N HCl, water
  6. customrecrystallized from an isopropanol-water mixture

Sources & evidence

ORD record
ord-6c86b073494c402984c16aa2acb7c96b
Source dataset
uspto-grants-1981_03
Patent number
US04255575

Reaction notes

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