Acetic Anhydride → 1-(3-Methylphenyl)-2-[2-(morpholin-4-yl)ethoxy]ethyl acetate

HRID 362953Notes

Reaction equation

HRID 362953 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][C:9]1[CH:10]=[C:11]([CH:15]([OH:26])[CH2:16][O:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:12]=[CH:13][CH:14]=1>N1C=CC=CC=1>[C:1]([O:26][CH:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([CH3:8])[CH:10]=1)[CH2:16][O:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 53902928HCID 53902928, compound

Product 1

HCID 30766181-(3-Methylphenyl)-2-[2-(morpholin-4-yl)ethoxy]ethyl acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.65 ml of pyridine and 0.99 ml of acetic anhydride were added to 1 g of 1-(3-methylphenyl)-2-[2-(morpholin-4-yl)ethoxy]ethanol. The mixture was stirred for 3 hours at room temperature. The reaction mixture was subjected to distillation under reduced pressure to remove the solvent. To the residue were added 20 ml of ethyl acetate and 10 ml of water. The mixture was adjusted to pH 10 with potassium carbonate. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: chloroform/ethanol=30/1) to obtain 1 g of oily 1-acetoxy-1-(3-methylphenyl)-2-[2-(morpholin-4-yl)ethoxy]ethane (compound No. 178).

Workup

  1. distillationThe reaction mixture was subjected to distillation under reduced pressure
  2. customto remove the solvent
  3. additionTo the residue were added 20 ml of ethyl acetate and 10 ml of water
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customThe residue was purified by column chromatography (eluant: chloroform/ethanol=30/1)

Sources & evidence

ORD record
ord-6f1c6efca022434c979ecddc083d02a6
Source dataset
uspto-grants-1999_02
Patent number
US05872117

Reaction notes

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