Water → 2,3-dihydro-1,4-benzodioxin-5-ylmethanol

HRID 2297567Notes

Reaction equation

HRID 2297567 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([C:17](OCC)=[O:18])[C:11]=2[O:10][CH2:9][CH2:8]1.O.[OH-].[Na+]>C(OCC)C>[OH:18][CH2:17][C:16]1[C:11]2[O:10][CH2:9][CH2:8][O:7][C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 18382450HCID 18382450, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 27761822,3-dihydro-1,4-benzodioxin-5-ylmethanolYield 88,496.898%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of lithium aluminum hydride (7.0 g, 0.18 mmol) in dry diethyl ether (100 mL) was added a solution of ethyl 1,4-benzodioxan-5-carboxylate (35 g, 0.17 mmol) in diethyl ether (100 mL). After boiling under reflux for 2 h, the reaction mixture was cooled to 0° C. and carefully treated with water (35 mL) and 4N aqueous sodium hydroxide (35 mL). The resulting mixture was filtered and dried (Na2SO4). Evaporation of the solvents afforded 25 g (88%) crystalline title compound: mp 51-53° C.; 1H NMR (CDCl3) δ 2.50 (s, 1H), 4.20-4.3 (m, 4H), 4.60 (s, 2H), 6.75-6.90 (m, 3H).

Workup

  1. temperatureunder reflux for 2 h
  2. filtrationThe resulting mixture was filtered
  3. dry with materialdried (Na2SO4)
  4. customEvaporation of the solvents

Sources & evidence

ORD record
ord-dc8fa778e77d4bd9be5edba78ad88921
Source dataset
uspto-grants-2002_12
Patent number
US06492374B2

Reaction notes

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