Chloroform → 2-Hydroxy-5-phenoxybenzaldehyde

HRID 892840Notes

Reaction equation

HRID 892840 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(Cl)(Cl)Cl.O.[CH2:22]([OH:24])C>>[OH:14][C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:13][C:12]=1[CH:22]=[O:24]

Participants

5

Reactant 4

HCID 6212ChloroformHCID 132544-PhenoxyphenolHCID 14798Sodium HydroxideHCID 19096565Water ethanol

Product 1

HCID 149712582-Hydroxy-5-phenoxybenzaldehyde

Conditions

Temperature
70 °C

Procedure

4-Phenoxyphenol (20.0 g, 107 mmol) and sodium hydroxide (3.8 g, 845 mmol) are dissolved in a water/ethanol (130 mL/26 mL) mixture and heated at 70° C. To this reaction mixture is added chloroform (24.6 g, 215 mmol) dropwise over 45 minutes, and heating is continued for 3 hours. The mixture is cooled to room temperature, and then evaporated. The aqueous phase is acidified with concentrated hydrochloric acid to pH 1-3, and extracted with ether. The organic phase is dried over magnesium sulfate and evaporated. Purification of the residue by silica-gel flash chromatography gives 2-hydroxy-5-phenoxybenzaldehyde as a yellow solid.

Workup

  1. temperatureheating
  2. temperatureThe mixture is cooled to room temperature
  3. customevaporated
  4. extractionextracted with ether
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. customevaporated
  7. customPurification of the residue by silica-gel flash chromatography

Sources & evidence

ORD record
ord-d437b3fcced94bc296576e2700334e36
Source dataset
uspto-grants-1992_06
Patent number
US05120758

Reaction notes

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