Hydrochloric Acid → (8-Methoxy-2,3-dihydro-1,4-benzodioxin-6-YL)methanol

HRID 2193128Notes

Reaction equation

HRID 2193128 reaction equation
O1CCCC1.[CH3:6][O:7][C:8]1[C:13]2[O:14][CH2:15][CH2:16][O:17][C:12]=2[CH:11]=[C:10]([C:18](OC)=[O:19])[CH:9]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O>[CH3:6][O:7][C:8]1[C:13]2[O:14][CH2:15][CH2:16][O:17][C:12]=2[CH:11]=[C:10]([CH2:18][OH:19])[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 18464946Methyl 8-Methoxy-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 16769335(8-Methoxy-2,3-dihydro-1,4-benzodioxin-6-YL)methanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 30 mL of a tetrahydrofuran solution containing 1.06 g of methyl 8-methoxy-2,3-dihydro-1,4-benzodioxin-6-carboxylate, 720 mg of lithium aluminum hydride was added under cooling with ice. The reaction mixture was stirred at room temperature for 1 hour, 5 mL of a 1 mol/L hydrochloric acid and 45 mL of water were added thereto, and the resultant solution was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 940 mg of a brown oily substance, (8-methoxy-2,3-dihydro-1,4-benzodioxin-6-yl)methanol.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. extractionthe resultant solution was extracted with ethyl acetate
  4. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-76315d6cdaa145ca955c4bd5ca3537e0
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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