Benzyl Alcohol → Ethyl 2-(benzyloxy)acetate

HRID 1774431Notes

Reaction equation

HRID 1774431 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].Cl>C1(C)C=CC=CC=1.O>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][O:10][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:17]

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydride

Product 1

HCID 290299Ethyl 2-(benzyloxy)acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a suspension of sodium hydride (44.2 g, 60 percent in oil, 1.1 mol) in dry toluene (800 mL) was added dropwise a solution of benzyl alcohol (108 mL, 1.0 mol, in 200 mL of toluene) at 0° C. under nitrogen over 30 min. The resulting mixture was stirred for 3.5 h at rt. The reaction was then cooled with ice water, to which a solution of ethyl bromoacetate (167.6 g, 1.0 mmol, in 200 mL of toluene) was added in 30 min and the resulting mixture was stirred for additional 25 min at 0° C. The reaction mixture was then poured into a mixed solution of 800 mL of cold water and 10 mL of cone HCl, followed by extraction with toluene. The organic layer was washed with saturated aq NaCl and dried over anhydrous MgSO4. Filtration, evaporation, and purification by flash chromatography provided ethyl(benzyloxy)acetate. (98 g, 50.5%). 1H-NMR δ (400 MHz, CDC3): 7.38-7.30 (m, 5H), 4.63 (s, 2H), 4.22 (q, J=7.2 Hz, 2H), 4.09 (s, 2H), 1.28 (t, J=7.2 Hz, 3H).

Workup

  1. additionwas added in 30 min
  2. stirringthe resulting mixture was stirred for additional 25 min at 0° C
  3. extractionfollowed by extraction with toluene
  4. washThe organic layer was washed with saturated aq NaCl
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationFiltration, evaporation, and purification by flash chromatography

Sources & evidence

ORD record
ord-0dc215b8bcf544558ae12e65e853090f
Source dataset
uspto-grants-2016_02
Patent number
US09260413B2

Reaction notes

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