Chloroform → 2-Hydroxy-5-phenoxybenzaldehyde

HRID 466177Notes

Reaction equation

HRID 466177 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>>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[C:12]([CH:13]=1)[CH:22]=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

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

Product 1

HCID 149712582-Hydroxy-5-phenoxybenzaldehyde

Conditions

Temperature
70 °C

Procedure

The starting material is prepared as follows: 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 conc. HCl to pH 1-3, and extracted twice with ether. The extracts are dried (MgSO4) and evaporated. Silica gel chromatography (10% ethyl acetate/hexane) of the residual oil yields 5-phenoxy-2-hydroxybenzaldehyde as a yellow solid, m.p. 54°-55° C., which is converted to 3-(N-hydroxyaminomethyl)-6-phenoxy-2H-1-benzopyran as described under (a).

Workup

  1. customThe starting material is prepared
  2. temperatureheating
  3. temperatureThe mixture is cooled to room temperature
  4. customevaporated
  5. extractionextracted twice with ether
  6. dry with materialThe extracts are dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-623b88feb2b944fa985d35f18dec9aac
Source dataset
uspto-grants-1992_10
Patent number
US05155130

Reaction notes

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