Potassium Carbonate → Methyl 3-methoxy-4-(2-methoxyethoxy)benzoate

HRID 871237Notes

Reaction equation

HRID 871237 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][CH2:16][O:17][CH3:18].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:6][O:5][C:4]1[CH:3]=[C:2]([CH:10]=[CH:9][C:7]=1[O:8][CH2:15][CH2:16][O:17][CH3:18])[C:1]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 19844Methyl VanillateHCID 809722-Bromoethyl methyl ether

Product 1

HCID 60351193Methyl 3-methoxy-4-(2-methoxyethoxy)benzoateYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl vanillate (6.376 g, 35 mmol), 1-bromo-2-methoxyethane (5.56 g, 40 mmol), and K2CO3 (5.528 g, 40 mmol) in DMF (40 mL) were reacted according to the procedure described in Example 6A Step 1, to afford methyl 3-methoxy-4-(2-methoxyethoxy)benzoate as a solid (8.394 g, 99.8%). 1H NMR (300 MHz, CDCl3) δ 7.65 (dd, 1H), 7.54 (d, 1H), 6.92 (d, 1H), 4.23 (q, 2H), 3.91 (s, 3H), 3.89 (s, 3H), 3.81 (t, 2H), 3.45 (s, 3H); LC-MS (ESI) m/z 241 (M+H)+.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-46780d6d55c6438db34af29a742f2ce1
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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