Citric Acid → HCID 18321330, compound

HRID 1699280Notes

Reaction equation

HRID 1699280 reaction equation
[CH3:1][C:2]([CH3:19])([O:4][C:5]([CH2:7][CH:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:6])[CH3:3].[H-].[Na+].[CH3:22][C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([CH3:31])[CH:30]=1)[CH2:26]Br.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.O>[CH2:17]([O:16][C:14]([C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])([CH2:22][C:23]1[CH:24]=[C:25]([CH3:26])[CH:28]=[C:29]([CH3:31])[CH:30]=1)[CH2:7][C:5]([O:4][C:2]([CH3:1])([CH3:3])[CH3:19])=[O:6])=[O:15])[CH3:18]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 1413343,5-Dimethylbenzyl bromideHCID 11346360diethyl [(1,1-dimethylethoxycarbonyl)methyl]-malonate

Product 1

HCID 18321330HCID 18321330, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 13.8 g (50.2 mMol) of diethyl [(1,1-dimethylethoxycarbonyl)methyl]-malonoate in 400 ml of anhydrous tetrahydrofuran, 2.3 g (52.7 mMol) of sodium hydride was added whilst being externally cooled with iced water. After stirring for 30 minutes, and maintaining a reaction temperature of 0 to +5° C., the solution of 10.0 g (50.2 mMol) of 3,5-dimethylbenzylbromide in 80 ml tetrahydrofuran was added dropwise and the mixture allowed to warm to room temperature within 14 hours. The reaction mixture was freed from the solvent in vacuo, 200 ml of 10% citric acid was added to the residue and the resulting mixture was thoroughly extracted with ethyl acetate. After the usual working up, the combined extracts yielded 19.7 g (100% of theory) of a colourless oil of Rf=0.67 (eluant: dichloromethane), which was used in the following steps without further purification.

Workup

  1. temperaturemaintaining a reaction temperature of 0 to +5° C.
  2. additionwas added to the residue
  3. extractionthe resulting mixture was thoroughly extracted with ethyl acetate
  4. customthe combined extracts yielded 19.7 g (100% of theory) of a colourless oil of Rf=0.67 (eluant: dichloromethane), which
  5. customwas used in the following steps without further purification

Sources & evidence

ORD record
ord-62aaae4af89d4b9cac0ac0dc88ab4f03
Source dataset
uspto-grants-2002_02
Patent number
US06344449B1

Reaction notes

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