Diethyl Malonate → HCID 19363381, compound

HRID 850479Notes

Reaction equation

HRID 850479 reaction equation
Br[C:2]1[C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:19]([O:27][CH2:28][CH3:29])(=[O:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].[H-].[Na+]>[Cu]Br.C1(C)C=CC=CC=1>[C:4]([C:3]1[C:2]([CH:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:19]([O:27][CH2:28][CH3:29])=[O:26])=[C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:9]([O:17][CH3:18])=[CH:8][CH:7]=1)([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 19363355HCID 19363355, compound2×

Product 1

HCID 19363381HCID 19363381, compound

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 1140TolueneSolvent

Procedure

2-bromo4-methoxy-3-pentyloxybenzoic acid (80.1 g, 253 mmol), toluene (480 ml), copper (I) bromide (3.62 g, 25.3 mmol) and diethyl malonate (153.4 ml, 1.01 mol) were mixed, and sodium hydride (60% dispersion, 30.3 g, 758 mmol) was added to this suspension. The mixture was stirred at 78° C.-83° C. for 1 hour. Said reaction mixture was combined with a reaction mixture in which 2-bromo-4-methoxy-3-pentyloxybenzoic acid (49.43 g, 156 mmol) had been reacted in the same manner, and the resulting reaction mixture was extracted with water (1000 ml, 500 ml). The aqueous layer was washed with hexane (500 ml). Concentrated hydrochloric acid was added to make the aqueous layer acidic. The aqueous layer was extracted with ethyl acetate (1000 ml, 500 ml). The organic layers were combined, and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure to give a crude product of diethyl 2-(6-carboxy-3-methoxy-2-pentyloxyphenyl)-malonate.

Workup

  1. customreaction mixture
  2. customhad been reacted in the same manner
  3. customthe resulting reaction mixture
  4. extractionwas extracted with water (1000 ml, 500 ml)
  5. washThe aqueous layer was washed with hexane (500 ml)
  6. additionConcentrated hydrochloric acid was added
  7. extractionThe aqueous layer was extracted with ethyl acetate (1000 ml, 500 ml)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationThe drying agent was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1b23e622592f41a59cab2ef98f0d61c7
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

Loading…