Dichloromethane → 3-Methoxyphenyl 3-oxo-3-(3,4,5-trimethoxyphenyl)propanoate

HRID 1020493Notes

Reaction equation

HRID 1020493 reaction equation
[O:1]=[C:2]([C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].[CH3:19][O:20][C:21]1[CH:22]=[C:23](O)[CH:24]=[CH:25][CH:26]=1.C(Cl)Cl>>[O:1]=[C:2]([C:7]1[CH:8]=[C:9]([O:17][CH3:18])[C:10]([O:15][CH3:16])=[C:11]([O:13][CH3:14])[CH:12]=1)[CH2:3][C:4]([O:6][C:25]1[CH:24]=[CH:23][CH:22]=[C:21]([O:20][CH3:19])[CH:26]=1)=[O:5]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 90073-MethoxyphenolHCID 148497283-Oxo-3-(3,4,5-trimethoxyphenyl)propionic acid

Product 1

HCID 672867273-Methoxyphenyl 3-oxo-3-(3,4,5-trimethoxyphenyl)propanoateYield 49%

Procedure

To a mixture of 0.27 g (1.06 mmol) of the product of Step 1 and 0.13 g (1.06 mmol) of 3-methoxyphenol in 2 ml of anhydrous methylenechloride 0.16 ml (1.06 mmol) of diisopropylcarbondiimide was added at room temperature. The resulting mixture was stirred for 24 hours at room temperature and filtered off. The filtrate was evaporated to dryness and purified by flash column chromaytography (silica gel; methylene chloride) to give the title compound as a colorless crystals (0.185 g, 49%); 1H NMR (CDCl3) δ 3.77 (s, 3H, OMe); 3.91 (s, 6H, OMe); 4.17 (s, 3H, OMe); 4.173 (s, 2H, CH2); 6.6-6.8 (m, 3H, CH aromatic); 7.2-7.3 (m, 3H, CH aromatic).

Workup

  1. additionwas added at room temperature
  2. filtrationfiltered off
  3. customThe filtrate was evaporated to dryness
  4. custompurified by flash column chromaytography (silica gel; methylene chloride)

Sources & evidence

ORD record
ord-bcabc62501ea45959533aacc82491d74
Source dataset
uspto-grants-2014_05
Patent number
US08716335B2

Reaction notes

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