Hydrochloric Acid → HCID 20480193, compound

HRID 1902750Notes

Reaction equation

HRID 1902750 reaction equation
Br[CH:2](Br)[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([O:15]C(=O)C)[CH:12]=[CH:11][C:10]=2[O:19]C(=O)C)=[CH:5][CH:4]=1.O.O.O.C([O-])(=[O:29])C.[Na+].CO.Cl>O>[CH:2]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=2[OH:19])=[CH:5][CH:4]=1)=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 20480191HCID 20480191, compoundHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 20480193HCID 20480193, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of about 4.4 g. (0.01 mole) of 4'-dibromomethyl-2,5-diacetoxy-1,1'-biphenyl, prepared as described in Example 2, and about 4.4 g. (0.03 mole) of sodium acetate trihydrate in a mixture of 50 ml. of methanol and 25 ml. of water was heated at reflux under nitrogen for about 4 hours. 5 ml. of concentrated hydrochloric acid were added and refluxing continued for an additional 11/2 hours. Most of the methanol was removed by evaporation on a steam bath under nitrogen resulting in precipitation of a light cream colored solid. The mixture was diluted with 50 ml. of water, cooled in an ice bath, and the resultant solid filtered, washed with water, and dried in a vacuum oven. Yield of about 2.0 g. of 4'-formyl-2,5-dihydroxy-1,1'-biphenyl, m.p. 203°-205° C. Thin layer chromatography indicated one component. Proton nuclear magnetic resonance and infrared spectra confirmed the structure and were essentially identical to the spectra obtained from the product of Example 3. The product gave a positive test with 2,4-dinitrophenylhydrazine spray reagent.

Workup

  1. additionA mixture of about 4.4 g
  2. temperatureat reflux under nitrogen for about 4 hours
  3. temperaturerefluxing
  4. custom2 hours
  5. customMost of the methanol was removed by evaporation on a steam bath under nitrogen resulting in precipitation of a light cream
  6. additionThe mixture was diluted with 50 ml
  7. temperatureof water, cooled in an ice bath
  8. filtrationthe resultant solid filtered
  9. washwashed with water
  10. customdried in a vacuum oven

Sources & evidence

ORD record
ord-9b90fa2b878248aca79f53dc64baa192
Source dataset
uspto-grants-1982_12
Patent number
US04365072

Reaction notes

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