Sodium Hydroxide → 2-Methoxyphenethyl alcohol

HRID 408491

Reaction equation

HRID 408491 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18].[OH-].[Na+]>O1CCCC1>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][CH2:9][OH:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 99590Methyl 2-methoxybenzeneacetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 819092-Methoxyphenethyl alcoholYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride (21 g, 0.55 mol) was added to a solution of (2-methoxy-phenyl)-acetic acid methyl ester (90 g, 0.50 mol) in anhydrous tetrahydrofuran (500 mL) at 0° C. After stirred at 0° C. for 30 minutes, the mixture was treated with sodium hydroxide (5% aqueous solution, 180 g). The mixture was extracted three times with ethyl acetate (400 mL) and the combined organic layers were washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered, and evaporated to dryness to give 2-(2-methoxy-phenyl)-ethanol (43 g, 0.28 mol, 57%), which was used directly in the next step.

Workup

  1. extractionThe mixture was extracted three times with ethyl acetate (400 mL)
  2. washthe combined organic layers were washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-46f5291157c747c4992affd6825b5387
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Linked notes

Loading…