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

HRID 484325Notes

Reaction equation

HRID 484325 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 characterized 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-d4bc44846a2d49549a5fc27384287a9f
Source dataset
uspto-grants-1993_07
Patent number
US05231104

Reaction notes

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