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Acetic Anhydride → 3-[p-[3-(2-Acetoxyethyl)oxy-2-methylpropionyl]benzyl]pyridine

HRID 569161
Notes
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Reaction equation

HRID 569161 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH:6]([CH3:22])[C:7]([C:9]1[CH:21]=[CH:20][C:12]([CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][CH:10]=1)=[O:8].[C:23](OC(=O)C)(=[O:25])[CH3:24]>N1C=CC=CC=1.C(OCC)(=O)C>[C:23]([O:1][CH2:2][CH2:3][O:4][CH2:5][CH:6]([CH3:22])[C:7]([C:9]1[CH:21]=[CH:20][C:12]([CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][CH:10]=1)=[O:8])(=[O:25])[CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 137455213-[p-[3-(2-Hydroxyethyl)oxy-2-methylpropionyl]benzyl]pyridine

Product 1

HCID 137455223-[p-[3-(2-Acetoxyethyl)oxy-2-methylpropionyl]benzyl]pyridine

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 3 ml of pyridine was dissolved 2.0 g of 3-[p-[3-(2-hydroxyethyl)oxy-2-methylpropionyl]benzyl]pyridine, and 0.76 ml of acetic anhydride was added to the resulting solution with ice-cooling, after which the resulting mixture was subjected to reaction at room temperature for 12 hours. The solvent was removed by distillation under reduced pressure, and the residue thus obtained was dissolved in 16 ml of ethyl acetate. The resulting solution was washed with 5 ml of water, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain crude oily 3-[p-[3-(2-acetoxyethyl)oxy-2-methylpropionyl]benzyl]pyridine. This was dissolved in 17 ml of ethanol.

Workup

  1. additionwas added to the resulting solution with ice-
  2. temperaturecooling
  3. customafter which the resulting mixture was subjected to reaction at room temperature for 12 hours
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe residue thus obtained
  6. washThe resulting solution was washed with 5 ml of water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-7ef5a5dfd8af47d1a9d5356901b249ee
Source dataset
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04731370

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes