Water → HCID 45094209, compound

HRID 1872699Notes

Reaction equation

HRID 1872699 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[O:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].I[CH2:21][CH3:22].O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:21][CH3:22])=[CH:6][C:5]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 12532676Methyl 4-hydroxy-2-methoxybenzoate

Product 1

HCID 45094209HCID 45094209, compoundYield 496.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-hydroxy-2-methoxybenzoic acid methyl ester (4.17 g, 22 mmol) in DMF (50 ml) under argon was added potassium carbonate (6.33 g, 4.6 mmol) followed by iodoethane (7.15 g, 4.6 mmol). The mixture was then heated to 50° C. under argon for 12h. On cooling the mixture was poured into a large excess of water and extracted with ether. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo to afford the title compound as a brown oil (4.8 g).

Workup

  1. temperatureOn cooling the mixture
  2. extractionextracted with ether
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54c18fb349834660834fe43df1b4f43d
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

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