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

HRID 1463881Notes

Reaction equation

HRID 1463881 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11](O)=[O:12])=[CH:4][C:3]=2[O:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH2:11][OH:12])=[CH:4][C:3]=2[O:2]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-olYield 90.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3,4-Methylenedioxyphenylacetic acid (18.0 g) was added portionwise over 30 minutes to a stirred, ice-cooled suspension of lithium aluminium hydride (4.0 g) in ether (400 ml) and the mixture was stirred at room temperature for two hours, quenched by the cautious addition of saturated aqueous ammonium chloride solution and filtered. The filtrate was washed with 10% aqueous sodium carbonate solution, dried over magnesium sulphate and evaporated to give the title compound as a pale yellow oil (15.01 g, 90%), which was characterised by its 1H-n.m.r. spectrum.

Workup

  1. temperaturecooled
  2. customquenched by the cautious addition of saturated aqueous ammonium chloride solution
  3. filtrationfiltered
  4. washThe filtrate was washed with 10% aqueous sodium carbonate solution
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-37963926744f48da9d21df5ad1fc4471
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

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