Ethyl Acetate → 1-(1,3-Dioxaindan-5-yl)ethan-1-ol

HRID 1364405Notes

Reaction equation

HRID 1364405 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:12])[CH3:11])=[CH:9][C:4]=2[O:3][CH2:2]1.[BH4-].[Na+].CC(=O)OCC>CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([OH:12])[CH3:11])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 76622AcetopiperoneHCID 4311764Sodium borohydride2×

Product 1

HCID 2218821-(1,3-Dioxaindan-5-yl)ethan-1-olYield 86.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-benzo[1,3]dioxol-5-yl-ethanone (2.5 gm; 15.2 mmol) in methanol (50 mL) is added sodium borohydride (634 mg; 16.7 mmol) in portions allowing for gas evolution. The reaction is stirred at room temperature for 3 hours before additional sodium borohydride is added to give a complete reaction by TLC (20% EA/Hex). The reaction is quenched with saturated ammonium chloride and extracted with ethyl acetate. The organics are separated, washed with water, dried over magnesium sulfate, and the solvent is removed to give 2.18 grams of 1-benzo[1,3]dioxol-5-yl-ethanol.

Workup

  1. additionis added
  2. customto give
  3. customThe reaction is quenched with saturated ammonium chloride
  4. extractionextracted with ethyl acetate
  5. customThe organics are separated
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent is removed

Sources & evidence

ORD record
ord-1b61cbba9714410682939e47db1a23a0
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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