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

HRID 1837797Notes

Reaction equation

HRID 1837797 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-adae64dff73944e19203460c737263b1
Source dataset
uspto-grants-2004_08
Patent number
US06784268B2

Reaction notes

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