Methanol → 4,7-Dimethoxy-1,3-dihydro-2-benzofuran-1-ol

HRID 437984Notes

Reaction equation

HRID 437984 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[CH2:5][O:6][C:7]2=[O:8].C(Cl)Cl.[H-].C([Al+]CC(C)C)C(C)C.CO>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[CH2:5][O:6][CH:7]2[OH:8]

Participants

7

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 37032364,7-DimethoxyphthalideHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 159144724,7-Dimethoxy-1,3-dihydro-2-benzofuran-1-ol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 6.19 g. of 4,7-dimethoxyphthalide in 500 ml. of methylene chloride which is cooled to -60° C. is added 48 ml. of diisobutylaluminum hydride in toluene and the mixture is stirred for one hour, 5 ml. of methanol is added and the solution is allowed to come to ambient temperature. The mixture is then treated with 600 ml. of chloroform and 300 ml. of sodium chloride solution and filtered. The organic layer is dried and the solvent removed to yield a white solid. This is washed with hexane to yield 4,7-dimethoxy-1,3-dihydro-1-isobenzofuranol having a melting point of 156°-158° C.

Workup

  1. additionis added 48 ml
  2. customto come to ambient temperature
  3. additionThe mixture is then treated with 600 ml
  4. filtrationof sodium chloride solution and filtered
  5. customThe organic layer is dried
  6. customthe solvent removed
  7. customto yield a white solid
  8. washThis is washed with hexane

Sources & evidence

ORD record
ord-d3be507384cb49be88eda90e17ed577b
Source dataset
uspto-grants-1977_06
Patent number
US04032656

Reaction notes

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