Isovanillic Acid → HCID 86610524, compound

HRID 495195Notes

Reaction equation

HRID 495195 reaction equation
[CH2:1]([C:3]1[C:8]([OH:9])=[CH:7][C:6]([OH:10])=[CH:5][C:4]=1[CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH3:2].[OH:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[C:20]([OH:22])=O>B(F)(F)F.CCOCC>[CH2:1]([C:3]1[C:8]([OH:9])=[CH:7][C:6]([OH:10])=[C:5]([C:20](=[O:22])[C:19]2[CH:23]=[CH:24][C:25]([O:26][CH3:27])=[C:17]([OH:16])[CH:18]=2)[C:4]=1[CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH3:2]

Participants

4

Reactant 2

HCID 12575Isovanillic AcidHCID 45093151HCID 45093151, compound

Product 1

HCID 86610524HCID 86610524, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8000Boron trifluoride etherateSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 2-ethyl-3,5-dihydroxyphenylacetate (2.0 g, 9.7 mmol) obtained in Example 7, Step 2 was suspended in boron trifluoride diethyl etherate (40 mL), and 3-hydroxy-4-methoxybenzoic acid (1.7 g, 11 mmol) was added thereto, followed by stirring at 80° C. for 5 hours. After cooling to room temperature, the reaction mixture was added dropwise to ice-cold water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4-9/1) to obtain methyl 2-ethyl-3,5-dihydroxy-6-(3-hydroxy-4-methoxybenzoyl)phenylacetate (2.2 g, 65%).

Workup

  1. temperatureAfter cooling to room temperature
  2. additionthe reaction mixture was added dropwise to ice-cold water
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with a saturated aqueous solution of sodium hydrogencarbonate
  5. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4-9/1)

Sources & evidence

ORD record
ord-7e53e9dbc8a94e30944eb6d50e91dd8c
Source dataset
uspto-grants-2009_05
Patent number
US07538224B2

Reaction notes

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