Ethyl Acetate → 2,3-Dihydro-1,4-benzodioxin-6-ol

HRID 394644Notes

Reaction equation

HRID 394644 reaction equation
C([O:4][C:5]1[CH:14]=[CH:13][C:8]2[O:9][CH2:10][CH2:11][O:12][C:7]=2[CH:6]=1)(=O)C.[OH-].[Na+].CCOC(C)=O>CO>[O:9]1[C:8]2[CH:13]=[CH:14][C:5]([OH:4])=[CH:6][C:7]=2[O:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 13470601HCID 13470601, compound

Product 1

HCID 91152732,3-Dihydro-1,4-benzodioxin-6-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 g of 2,3-dihydro-1,4-benzodioxin-6-yl acetate (5.149 mmol) is dissolved in a solution of methanol (7.5 ml) and, under an argon atmosphere, the mixture is made basic, dropwise, with a 10% sodium hydroxide solution. The mixture is stirred at ambient temperature for 4 hours. At the end of the reaction, the methanol is evaporated and the reaction medium is acidified (to pH=1) with a 2N HCl solution and then washed with ethyl acetate. After extraction, drying over MgSO4 is carried out and the product is concentrated in vacuo. Purification on a silica column allows an oil to be obtained (eluant: PE/AcOEt 8/2 then 7/3).

Workup

  1. customAt the end of the reaction
  2. customthe methanol is evaporated
  3. washwashed with ethyl acetate
  4. extractionAfter extraction
  5. dry with materialdrying over MgSO4
  6. concentrationthe product is concentrated in vacuo
  7. customPurification on a silica column
  8. customto be obtained (eluant

Sources & evidence

ORD record
ord-1d25d51449cf44ec839be933785bf6bb
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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