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Acetaminophen → 6-(4-Acetylaminophenoxy)-hexanoic acid methyl ester

HRID 83786
Notes
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Reaction equation

HRID 83786 reaction equation
[NH:1]([C:5]1[CH:11]=[CH:10][C:8]([OH:9])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].C([O-])([O-])=O.[K+].[K+].[I-].[Na+].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27]>CC(C)=O>[CH3:29][O:28][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][O:9][C:8]1[CH:10]=[CH:11][C:5]([NH:1][C:2](=[O:3])[CH3:4])=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1983AcetaminophenHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 4170292Methyl 6-Bromohexanoate

Product 1

HCID 497644916-(4-Acetylaminophenoxy)-hexanoic acid methyl esterYield 42,206.5%

Reagents, catalysts & solvents 1

HCID 180
Acetone
Solvent

Procedure

To a mixture of paracetamol (250 gm, 1.654 mmol), anhydrous K2CO3 (800 gm, 5.789 mmol) and sodium iodide (17 g, 113 mmol) in anhydrous acetone (5 L) was added methyl 6-bromohexanoate (470 g, 2.25 mmol) and refluxed for 60 hours. Acetone was distilled off and water (3 L) was added. Crude 15 was filtered, dried and recrystallised from a mixture of chloroform:hexane (1:5) to give pure 15 (195 g, 66%) as a white powder with an m.p between 96.4-98.8° C.

Workup

  1. temperaturerefluxed for 60 hours
  2. distillationAcetone was distilled off
  3. additionwater (3 L) was added
  4. filtrationCrude 15 was filtered
  5. customdried
  6. customrecrystallised from a mixture of chloroform:hexane (1:5)

Sources & evidence

ORD record
ord-d6672ac9b2414dc78a3e6a392bd4b291
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846845B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes