Hydrochloric Acid → 78725-45-8

HRID 440575Notes

Reaction equation

HRID 440575 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[Cl:10][C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1.[H-].[Na+].Cl>N1C=CC=CC=1.O>[Cl:10][C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[O:17][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 79333-ChlorophenolHCID 24758Sodium hydrideHCID 765833-Bromobenzaldehyde

Product 1

HCID 1581876078725-45-8

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A mixture of 3-bromobenzaldehyde (6.0g), 3-Chlorophenol (4.8g), sodium hydride (1.3 g of an 80% suspension in oil) and cuprous cloride (1 g) was heated under reflux in pyridine (125 ml) under an atmosphere of nitrogen gas for 16 hours. The mixture was cooled, diluted with water, acidified with hydrochloric acid and extracted with diethyl ether. The etheral extracts were dried (Na2SO4), concentrated and purified by chromatography on silica gel eluting with ethyl acetate-petroleum ether (1:9) to give the title compound as a colourless oil.

Workup

  1. temperaturewas heated
  2. temperatureThe mixture was cooled
  3. extractionextracted with diethyl ether
  4. dry with materialThe etheral extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by chromatography on silica gel eluting with ethyl acetate-petroleum ether (1:9)

Sources & evidence

ORD record
ord-6b81b45010e14d128110c98cb2333c52
Source dataset
uspto-grants-1996_05
Patent number
US05519163

Reaction notes

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