Acetic Acid → HCID 22857727, compound

HRID 2259513Notes

Reaction equation

HRID 2259513 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C@H:10]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[CH:20]=1)[O:11][CH2:12][C:13]1(CC#N)[CH2:15][CH2:14]1.[OH-].[K+].CCO.[CH3:38][C:39]([OH:41])=[O:40]>CCOC(C)=O.C1(C)C=CC=CC=1.CC(O)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C@H:10]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[CH:20]=1)[O:11][CH2:12][C:13]1([CH2:38][C:39]([OH:41])=[O:40])[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 22857728HCID 22857728, compound

Product 1

HCID 22857727HCID 22857727, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 21906519HCID 21906519, compoundSolvent

Procedure

A mixture of the nitrile of Step 6 (13.22 g, 26.5 mmol), 8N KOH (330 mL), and EtOH (130 mL) was heated to reflux for 17 hr. 25% Aq. NH4OAc (500 mL) and AcOH (190 mL) were than added at room temperature (to give pH~6) and the product was extracted in EtOAc and dried over Na2SO4. Hash chromatography of the residue with EtOAc:toluene:AcOH 10:90:1 afforded 10.34 g (75% yield) of the title acid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 17 hr
  3. additionthan added at room temperature
  4. custom(to give pH~6)
  5. extractionthe product was extracted in EtOAc
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-e6b06a2777314263939a025c8c203fb8
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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