Hydrochloric Acid → 1,3-Benzodioxole-5-propanol

HRID 890818Notes

Reaction equation

HRID 890818 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][CH2:17][C:18](O)=[O:19])=[CH:15][C:10]=2[O:9][CH2:8]1.Cl>C1COCC1>[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][CH2:17][CH2:18][OH:19])=[CH:15][C:10]=2[O:9][CH2:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 648103-(Benzodioxol-5-yl)propionic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 110304141,3-Benzodioxole-5-propanolYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (1M in THF, 30 mL, 30 mmol) was added slowly to a solution of 3-benzo[1,3]dioxol-5-yl-propionic acid (5.83 g, 30 mmol) in THF (60 mL) at 0° C. The reaction was warmed to room temperature and was stirred for 2 h. The solution was added in portions to a mixture of ice (200 g) and concentrated HCl (2 mL). The product was extracted into EtOAc. The organic solution was dried over MgSO4, filtered, and concentrated. Purification by flash chromatography (hexanes:EtOAc 6:4) provided the title alcohol (4.51 g). 1H NMR (400 MHz, CDCl3) δ 6.73–6.62 (m, 3H), 5.91 (s, 2H), 3.66 (t, 2H), 2.63 (t, 2H), 1.84 (m, 2H).

Workup

  1. extractionThe product was extracted into EtOAc
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromatography (hexanes:EtOAc 6:4)

Sources & evidence

ORD record
ord-06da0d919a7f4a8690191d2ec18b6d0d
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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