Potassium Carbonate → HCID 57791081, compound

HRID 1158330Notes

Reaction equation

HRID 1158330 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([OH:12])[CH:5]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:21][CH2:22][CH2:23][O:24][CH3:25]>CC#N>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH2:21][CH2:22][CH2:23][O:24][CH3:25])[CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5245511-Bromo-3-methoxypropaneHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 57791081HCID 57791081, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of methyl-3-hydroxy-4-methoxybenzoate (Aldrich) (89.3 g, 0.49 mol), K2CO3 (100.5 g, 0.727 mol) and 1-bromo-3-methoxy-propane (80 g, 0.523 mol) in CH3CN (1100 mL) is refluxed for 6 h. After completion of the reaction, the mixture is cooled to RT and concentrated under reduced pressure. The residue is taken up into AcOEt (500 mL) and washed with water. The aqueous layer is back-extracted twice with AcOEt, and the combined organic extracts are dried over MgSO4, filtered and concentrated to afford the title compound which is further used in the next step without purification. tR (HPLC, CC 70/4 Nucleosil 3 C18HD column, 20 to 100% CH3CN in H2O in 2, then 4 min with 100% CH3CN, CH3CN and H2O with 0.1% TFA, flow: 1.5 mL/min): 3.07 min.

Workup

  1. customAfter completion of the reaction
  2. concentrationconcentrated under reduced pressure
  3. washwashed with water
  4. extractionThe aqueous layer is back-extracted twice with AcOEt
  5. dry with materialthe combined organic extracts are dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d766a30834a0437b9a2813339f65c5d4
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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