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

HRID 2176985Notes

Reaction equation

HRID 2176985 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-0ce74a4ff9aa416ab0e902f10e103684
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

Loading…