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

HRID 39757Notes

Reaction equation

HRID 39757 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-3a1e10de7d8d4e789b490a43f855051d
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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