Dimethyl Succinate → HCID 54348894, compound

HRID 1067306Notes

Reaction equation

HRID 1067306 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1)[CH:12]=O.[C:19]([O:27]C)(=[O:26])[CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23].C(OC(C)C)(C)C>C(O)(C)(C)C.O1CCCC1.O>[CH3:25][O:24][C:22](=[O:23])[CH2:21][C:20]([C:19]([OH:27])=[O:26])=[CH:12][C:11]1[CH:10]=[C:9]([O:8][CH3:7])[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=1

Participants

8

Reactant 4

HCID 7820Dimethyl SuccinateHCID 7914Diisopropyl EtherHCID 817473,5-DimethoxybenzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 54348894HCID 54348894, compoundYield 124.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (14.2 g) is dissolved in tert-butyl alcohol (120 ml), and thereto is added dropwise a solution of 3,5-dimethoxybenzaldehyde (20 g) and dimethyl succinate (21.1 g) in tetrahydrofuran. The mixture is stirred at room temperature for 30 minutes, and water and isopropyl ether are added to the mixture. The aqueous layer is separated, and the remaining organic layer is further extracted with water. The aqueous layers are combined, and the pH value thereof is adjusted to pH 2-3 with conc. hydrochloric acid. The resulting oily product is extracted with ethyl acetate, and the extract is dried, concentrated under reduced pressure to give 4-(3,5-dimethoxyphenyl)-3-carboxy-3-butenoic acid methyl ester (42 g) as an oily product.

Workup

  1. customThe aqueous layer is separated
  2. extractionthe remaining organic layer is further extracted with water
  3. extractionThe resulting oily product is extracted with ethyl acetate
  4. customthe extract is dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b90867a062d4456380c582a12860ed41
Source dataset
uspto-grants-2001_06
Patent number
US06248743B1

Reaction notes

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