Water → 5-(1-Acetoxy-5-methoxypentyl)-2-norbornene

HRID 1168617Notes

Reaction equation

HRID 1168617 reaction equation
[OH:1][CH:2]([CH:9]1[CH2:14][CH:13]2[CH2:15][CH:10]1[CH:11]=[CH:12]2)[CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH3:8].[C:16](OC(=O)C)(=[O:18])[CH3:17].O>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:16]([O:1][CH:2]([CH:9]1[CH2:14][CH:13]2[CH2:15][CH:10]1[CH:11]=[CH:12]2)[CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH3:8])(=[O:18])[CH3:17]

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 226790435-(1-Hydroxy-5-methoxypentyl)-2-norbornene2×

Product 1

HCID 226790425-(1-Acetoxy-5-methoxypentyl)-2-norborneneYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

In 63.3 g of pyridine, 105.2 g of 5-(1-hydroxy-5-methoxypentyl)-2-norbornene (Monomer 1) was reacted with 61.3 g of acetic anhydride in the presence of 2 g of 4-dimethylaminopyridine at room temperature for 10 hours. The reaction was stopped by adding 30 g of water. Extraction with hexane gave the organic layer, which was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuum. The oily matter thus obtained was distilled in vacuum, obtaining 122.4 g of 5-(1-acetoxy-5-methoxypentyl)-2-norbornene. The yield was 97.0%.

Workup

  1. extractionExtraction with hexane
  2. customgave the organic layer, which
  3. washwas washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe oily matter thus obtained
  8. distillationwas distilled in vacuum

Sources & evidence

ORD record
ord-cd8ecfd1eea34c418da7430bc9694d88
Source dataset
uspto-grants-2003_09
Patent number
US06624335B2

Reaction notes

Loading…