Citric Acid → HCID 68480331, compound

HRID 1513996Notes

Reaction equation

HRID 1513996 reaction equation
C[O-].[Na+].[C:4]([O:11][CH3:12])(=[O:10])[CH2:5][C:6]([O:8][CH3:9])=[O:7].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH3:9][O:8][C:6]([CH:5]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:4]([O:11][CH3:12])=[O:10])=[O:7]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 7943Dimethyl malonateHCID 10942334Sodium MethoxideHCID 11495516(6-Bromohexyloxy)triphenylmethane

Product 1

HCID 68480331HCID 68480331, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (1.42 g, 26.2 mmol) was dissolved in dry MeOH (90 mL). Dimethyl malonate (3.0 mL, 26.2 mmol) was added and the mixture was stirred at r.t. for one hour. (6-Bromohexyloxy)triphenylmethane (3.7 g, 8 7 mmol) was added and the mixture was refluxed overnight. The mixture was cooled to r.t. and 50 mL 10% citric acid was added. The mixture was then stirred at r.t. for 5 min. The product was extracted with CH2Cl2 (3×100 mL) and evaporated to dryness. The residue was dissolved in CH2Cl2 and dried with Na2SO4. Purification on silica gel (petroleum ether, by 40-60° C./ethyl acetate 10:1) yielded 2.3 g (56%) of the title compound. ESI-TOF-MS [M+Na]+: calc. for C30H34NaO5+ 497.23. found 497.17.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. temperatureThe mixture was cooled to r.t.
  3. stirringThe mixture was then stirred at r.t. for 5 min
  4. extractionThe product was extracted with CH2Cl2 (3×100 mL)
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in CH2Cl2
  7. dry with materialdried with Na2SO4
  8. customPurification on silica gel (petroleum ether, by 40-60° C./ethyl acetate 10:1)

Sources & evidence

ORD record
ord-19b6754fa1284187909391438d9e8000
Source dataset
uspto-grants-2012_07
Patent number
US08221719B2

Reaction notes

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