Hydrochloric Acid → 3-Methyl-6-hydroxybenzofuran

HRID 1107864Notes

Reaction equation

HRID 1107864 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH2:6][C:7](=O)[CH3:8].[OH-].[K+].Cl>>[CH3:8][C:7]1[C:10]2[CH:11]=[CH:12][C:2]([OH:1])=[CH:3][C:4]=2[O:5][CH:6]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 18786125(3-Hydroxyphenoxy)acetone

Product 1

HCID 108556243-Methyl-6-hydroxybenzofuranYield 60.4%

Conditions

Temperature
5 °C

Procedure

3 g (18 mmol) of (3-hydroxyphenoxy)acetone and 400 ml of a 0.1M potassium hydroxide solution are introduced into a 1 l three-necked flask equipped with a reflux condenser. Heating is carried out at reflux for 6 hours. The reaction mixture is cooled to 5° C., a molar hydrochloric acid solution is added, in order to obtain a pH of approximately 5, and extraction is carried out with ethyl ether (3×150 ml). The organic phases are combined, dried over magnesium sulphate and concentrated. The residue is purified by silica column chromatography (elution solvent: 8/2 cyclohexane/ethyl acetate). 1.61 g of 3-methyl-6-hydroxybenzofuran are obtained--M.p.: 92° C.

Workup

  1. customequipped with a reflux condenser
  2. temperatureHeating
  3. temperatureat reflux for 6 hours
  4. customto obtain
  5. extractiona pH of approximately 5, and extraction
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated
  8. customThe residue is purified by silica column chromatography (elution solvent: 8/2 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-80cae4e0f7424c6ea2f4512a170fc7a7
Source dataset
uspto-grants-2000_05
Patent number
US06063810

Reaction notes

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