Pyridine → HCID 15229503, compound

HRID 1646813Notes

Reaction equation

HRID 1646813 reaction equation
[OH:1][CH:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].[C:18](OC(=O)C)(=[O:20])[CH3:19].N1C=CC=CC=1.CN(C1C=CC=CN=1)C>ClCCl>[C:18]([O:1][CH:2]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 19088023HCID 19088023, compound

Product 1

HCID 15229503HCID 15229503, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-Hydroxy-8-phenyloctanoic acid (25 g) was dissolved in dichloromethane (100 ml), and acetic anhydride (12 ml), pyridine (25 ml) and dimethylaminopyridine (0.1 g) were added to the solution, followed by stirring at room temperature for 3 hours. The reaction solution was washed with water and then twice with 2N hydrochloric acid, and the organic layer was washed with water, dried and concentrated under reduced pressure to give 8-acetoxy-8-phenyloctanoic acid (21 g). Its typical physical properties and nuclear magnetic resonance spectrum are shown in Table 13.

Workup

  1. washThe reaction solution was washed with water
  2. washtwice with 2N hydrochloric acid, and the organic layer was washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-854c93949a3e4689a1fff8093a305475
Source dataset
uspto-grants-1993_01
Patent number
US05180742

Reaction notes

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