Hydrochloric Acid → 1-(4-Bromophenyl)-2-hydroxy-2-p-tolylethanone

HRID 1284282Notes

Reaction equation

HRID 1284282 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]=[O:11])=[O:9])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH:10]([C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)[OH:11])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2335862-(4-Bromophenyl)-2-oxoacetaldehydeHCID 6451240Aluminum(III) Chloride

Product 1

HCID 203722961-(4-Bromophenyl)-2-hydroxy-2-p-tolylethanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 67 g. (0.314 mole) of p-bromophenyl-glyoxal in 300 ml. of dry toluene is added dropwise over 1 1/2 hours to a stirred suspension of 84 g. (0.6 mole) of anhydrous aluminum chloride in 1.25 l. of dry toluene cooled in an ice-bath. Stirring in the cold is continued for 5 hours and the mixture then is held at 5°-10°C. overnight. The mixture is poured into about 2 l. of ice and 6N hydrochloric acid. The aqueous phase is separated and re-extracted with three portions of benzene. The combined, washed and dried organic extracts are concentrated under reduced pressure to a volume of about 200 ml. Dilution with 150 ml. of petroleum ether precipitates the white crystalline product, m.p. 80°-82°C. Repeated recrystallization from 60% ethanol affords the analytical sample, m.p. 82°-83.5°C.

Workup

  1. waitthe mixture then is held at 5°-10°C. overnight
  2. additionThe mixture is poured into about 2 l
  3. customThe aqueous phase is separated
  4. extractionre-extracted with three portions of benzene
  5. washwashed
  6. concentrationdried organic extracts are concentrated under reduced pressure to a volume of about 200 ml
  7. customof petroleum ether precipitates the white crystalline product, m.p. 80°-82°C
  8. customrecrystallization from 60% ethanol
  9. customaffords the analytical sample, m.p. 82°-83.5°C.

Sources & evidence

ORD record
ord-9d4402a11cc64c9696b16e7ed40c9a92
Source dataset
uspto-grants-1976_08
Patent number
US03978127

Reaction notes

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