Benzo-1,3-dioxole-5-acetic acid → 2-(1,3-Dioxaindan-5-yl)ethan-1-ol

HRID 1489188Notes

Reaction equation

HRID 1489188 reaction equation
[C:1]([CH2:4][C:5]1[CH:13]=[CH:12][C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=1)(O)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[OH:2][CH2:1][CH2:4][C:5]1[CH:13]=[CH:12][C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 76115Benzo-1,3-dioxole-5-acetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 27598462-(1,3-Dioxaindan-5-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5-Carboxymethyl-1,3-benzodioxolane (18 g) was added, in portions over 30 minutes, to a stirred, ice-cooled (0° C.) suspension of lithium aluminium hydride (4 g) in diethyl ether (400 ml). The mixture was stirred at room temperature for 2 hours then quenched by the cautious addition of saturated aqueous ammonium chloride solution. The mixture was filtered and the filtrate was washed with 10% aqueous sodium carbonate solution then dried (MgSO4) and concentrated in vacuo to give the title compound as an oil, 15.01 g.

Workup

  1. temperaturecooled
  2. customthen quenched by the cautious addition of saturated aqueous ammonium chloride solution
  3. filtrationThe mixture was filtered
  4. washthe filtrate was washed with 10% aqueous sodium carbonate solution
  5. dry with materialthen dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eba4e19291f04afda7bf95bdb70dbae0
Source dataset
uspto-grants-1997_10
Patent number
US05677324

Reaction notes

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