Acetic Anhydride → HCID 18182171, compound

HRID 1359259Notes

Reaction equation

HRID 1359259 reaction equation
[OH:1][CH:2]([C:9]1[CH:14]=[CH:13][N:12]=[C:11]([O:15][CH3:16])[CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>N1C=CC=CC=1>[C:17]([O:1][CH:2]([C:9]1[CH:14]=[CH:13][N:12]=[C:11]([O:15][CH3:16])[CH:10]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 181824412-Methoxy-α-phenyl-4-pyridinemethanol

Product 1

HCID 18182171HCID 18182171, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 104 g of 4-(α-hydroxybenzyl)-2-methoxypyridine, 100 ml of acetic acid anhydride and 100 ml of pyridine was heated under stirring for 5 hours in an oil bath kept at 110° C. After the reaction solution was evaporated, water was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed with an aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 5-20% ethyl acetate/hexane, to give 112 g of the target compound.

Workup

  1. temperaturewas heated
  2. customkept at 110° C
  3. customAfter the reaction solution was evaporated
  4. additionwater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with an aqueous sodium bicarbonate solution and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-ca3880a2a0fd48c1b21950925e7f6896
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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