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

HRID 1192002Notes

Reaction equation

HRID 1192002 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-cb0729c1809447c88b56d725553eb8a0
Source dataset
uspto-grants-2014_03
Patent number
US08680135B2

Reaction notes

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