Citric Acid → HCID 12906308, compound

HRID 1893508Notes

Reaction equation

HRID 1893508 reaction equation
[C:1]1([CH2:9]Br)[C:2]([CH2:7]Br)=[CH:3][CH:4]=[CH:5][CH:6]=1.C([N:13](CC)CC)C.C(O)(=O)[CH2:19][C:20]([CH2:25]C(O)=O)([C:22](O)=O)[OH:21].[CH3:31][N:32]1CCC[C:33]1=[O:37]>>[CH2:7]1[C:2]2[C:1](=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][N:13]1[N:32]([CH3:31])[C:33](=[O:37])[O:21][C:20]([CH3:19])([CH3:22])[CH3:25]

Participants

5

Reactant 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 66665o-Bis(bromomethyl)benzene

Product 1

HCID 12906308HCID 12906308, compoundYield 84%

Procedure

The step was performed according to the method described in U.S. Pat. No. 4,272,284. Xylylene dibromide (160 g, 606 mmol) and compound (88.52 g, 606 mmol) obtained in step A were dissolved in N-methylpyrrolidone (550 ml). While maintaining the reaction mixture at 50° C.-60° C., triethylamine (190 ml, 1.36 mol) was gradually added dropwise using infundibulum with stirring and, after the completion of the dropwise addition, the reaction mixture was stood overnight at room temperature. A 5% aqueous citric acid solution (700 ml) was added to the reaction mixture, and the precipitated solid was collected by filtration, washed with water and dried under reduced pressure to give the title compound (126 g, yield 84%) as a crude pale-pink solid.

Workup

  1. temperatureWhile maintaining the reaction mixture at 50° C.-60° C.
  2. additionafter the completion of the dropwise addition
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-584f233c40a14c53a81d412dccd55c02
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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