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Benzyl Chloride → HCID 57572477, compound

HRID 1038287
Notes
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Reaction equation

HRID 1038287 reaction equation
[OH:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]([C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[C:14]([OH:16])=[O:15].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:17]([O:9][C:8]([C:7]1[CH:6]=[C:5]([C:11]([O:13][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:12])[CH:4]=[C:3]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[C:2]=1[O:1][CH2:14][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1)=[O:10])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 234240322-Hydroxy-1,3,5-benzenetricarboxylic acid

Product 1

HCID 57572477HCID 57572477, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Compound 13 (22.6 g, 0.1 mol), benzyl chloride (57 g, 0.46 mol) and anhydrous potassium carbonate (120 g, 0.87 mol) were mixed in dry DMF (500 mL). The mixture was heated at 75° C. while stirring under nitrogen overnight. TLC confirmed that the reaction was complete. The reaction mixture was cooled, filtered, and the filtrate was evaporated to remove the volatiles. The residue was dissolved in 1 L of recycling [?] methylene chloride and a silica gel plug was used to remove some impurities with low Rf. The fully benzyl-protected product was obtained as a thick, yellow oil after removing the solvent: raw yield 53 g (90%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate was evaporated
  4. customto remove the volatiles
  5. dissolutionThe residue was dissolved in 1 L
  6. customto remove some impurities with low Rf
  7. customwas obtained as a thick, yellow oil
  8. customafter removing the solvent

Sources & evidence

ORD record
ord-51a40e008c1745f58a07f42d6a361044
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08551453B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes