Acetone → 3-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic Acid

HRID 659312Notes

Reaction equation

HRID 659312 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH:15]([C:16]([O:18]C)=[O:17])C3C=C(C=CC(OC)=O)C=C(OC)C=3O2)[CH:6]=[CH:7][C:8]=1[O:9]C.CC(C)=O.[OH-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[OH:9])[CH:11]=[CH:15][C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 5225571HCID 5225571, compound

Product 1

HCID 7093-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic AcidYield 330.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1 g of methyl 3-[2-(3,4-dimetoxyphenyl)-7-methoxy-3-methoxycarbonyl-2,3-dihydro -1-benzofuran-5-yl]prop-2-enoate, 10 mL of acetone and 2.5 mL of water were mixed and stirred to dissolve. Then, 3% NaOH (6 mL) was added to the mixture and stirred for 0.5 hr. After reaction completed, the mixture was acidified and purified by chromatography on silica gel column with a 1:2:0.8 V/V mixture of petroleum ether, ethyl acetate and acetic acid as eluent. After removing solvent, it gave 1.5 g yellow solid of 5-[(E)-2-carboxyethenyl]-2-(3,4-dimetoxyphenyl)-2,3-dihydro-7-methoxy-3-benzofurancarboxylic acid (IM2).

Workup

  1. dissolutionto dissolve
  2. stirringstirred for 0.5 hr
  3. customAfter reaction
  4. custompurified by chromatography on silica gel column with a 1:2
  5. addition0.8 V/V mixture of petroleum ether, ethyl acetate and acetic acid as eluent
  6. customAfter removing solvent, it

Sources & evidence

ORD record
ord-57e80c8c174047ccaa0e298a3beed521
Source dataset
uspto-grants-2011_12
Patent number
US08080582B2

Reaction notes

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