Ethyl Bromide → Methyl 4-ethoxy-3-methoxybenzoate

HRID 1917630Notes

Reaction equation

HRID 1917630 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.Br[CH2:15][CH3:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:15]([O:8][C:7]1[CH:9]=[CH:10][C:2]([C:1]([O:12][CH3:13])=[O:11])=[CH:3][C:4]=1[O:5][CH3:6])[CH3:16]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 19844Methyl Vanillate

Product 1

HCID 592192Methyl 4-ethoxy-3-methoxybenzoateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl vanillate (6.376 g, 35 mmol), bromoethane (4.359 g, 40 mmol), and K2CO3 (5.528 g, 40 mmol) in DMF (40 mL) was heated at 70° C. for 2 hours. The reaction mixture was quenched with water, filtered, washed with water, and dried under vacuum with P2O5 to give methyl 4-ethoxy-3-methoxybenzoate as white solid (7.123 g, 97%). 1H NMR (300 MHz, CDCl3) δ 7.66 (dd, 1H), 7.55 (d, 1H), 6.88 (d, 1H), 4.17 (q, 2H), 3.93 (s, 3H), 3.89 (s, 3H), 1.50 (t, 3H); LC-MS (ESI) m/z 211 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with water
  2. filtrationfiltered
  3. washwashed with water
  4. dry with materialdried under vacuum with P2O5

Sources & evidence

ORD record
ord-32b79552fffa4b9aa5acfab1773051ae
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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