Hydrochloric Acid → 6-Hydroxybenzofuran

HRID 2118093Notes

Reaction equation

HRID 2118093 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[CH:6](O)[CH2:7][O:8][C:4]=2[CH:3]=1.Cl>C1COCC1.[Cl-].[Na+].O>[O:8]1[C:4]2[CH:3]=[C:2]([OH:1])[CH:11]=[CH:10][C:5]=2[CH:6]=[CH:7]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18414573HCID 18414573, compound

Product 1

HCID 1288446-Hydroxybenzofuran

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of 6-hydroxy-2,3-dihydrobenzofuran-3-ol (35.2 g, 0.2 mol) in THF (1.3 L) was added hydrochloric acid (323 mL, 1.0 N). The mixture was stirred at 65° C. for 2 h. After cooling to room temperature, it was diluted with brine (2.0 L), extracted with ethyl acetate (4.0 L), dried over magnesium sulfate, filtered and concentrated. The crude product was purified on a silica gel column, eluting with ethyl acetate (1-30%) in heptane. The final product was collected as light brown solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate (4.0 L)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified on a silica gel column
  7. washeluting with ethyl acetate (1-30%) in heptane
  8. customThe final product was collected as light brown solid

Sources & evidence

ORD record
ord-f510cbd39b2643eb91156f8df2272da5
Source dataset
uspto-grants-2008_10
Patent number
US07442808B2

Reaction notes

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