Hydrochloric Acid → 3-Methyl-1-benzofuran-5-ol

HRID 1504258Notes

Reaction equation

HRID 1504258 reaction equation
[CH3:1][CH:2]1[C:6]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=2[O:4][CH:3]1N1CCOCC1.Cl>>[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 138729953-Methyl-2-(morpholin-4-yl)-2,3-dihydro-1-benzofuran-5-ol

Product 1

HCID 135425263-Methyl-1-benzofuran-5-olYield 74.1%

Conditions

Temperature
56 °C

Procedure

3-Methyl-2-morpholin-4-yl-2,3-dihydro-benzofuran-5-ol (prepared as above in EXAMPLE II) (628 g, 2.7 mol) was added to hydrochloric acid (HCl) (20%, 2 L) at room temperature with stirring. The reaction mixture was heated to 56° C. for 3 hours and then cooled down. The crude was extracted with toluene (500 mL) for three times. The organic phases were obtained, combined and evaporated to provide a crude product, which was further recrystallization to afford 3-methyl-benzofuran-5-ol (290 g, 2 mol).

Workup

  1. temperaturecooled down
  2. extractionThe crude was extracted with toluene (500 mL) for three times
  3. customThe organic phases were obtained
  4. customevaporated
  5. customto provide a crude product, which
  6. customrecrystallization

Sources & evidence

ORD record
ord-4dea6fb1594e4fd7bd3c6129ba2a0cab
Source dataset
uspto-grants-2015_12
Patent number
US09212336B2

Reaction notes

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