Hydrochloric Acid → 5-(1-Hydroxy-5-methoxypentyl)-2-norbornene

HRID 1168616Notes

Reaction equation

HRID 1168616 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH3:7].[Mg].[CH:9]12[CH2:15][CH:12]([CH:13]=[CH:14]1)[CH2:11][CH:10]2[CH:16]=[O:17].Cl>O1CCCC1.O>[OH:17][CH:16]([CH:10]1[CH2:11][CH:12]2[CH2:15][CH:9]1[CH:14]=[CH:13]2)[CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH3:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 873631-Chloro-4-methoxybutaneHCID 95117Bicyclo(2.2.1)hept-5-ene-2-carboxaldehydeHCID 5462224Magnesium

Product 1

HCID 226790435-(1-Hydroxy-5-methoxypentyl)-2-norborneneYield 75.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 300 g of tetrahydrofuran was dissolved 122.6 g of 1-chloro-4-methoxybutane. The solution was added dropwise to 24.3 g of metallic magnesium over 2 hours and below 60° C. Agitation was continued for 2 hours at room temperature. To the solution, 122.2 g of 5-norbornene-2-carbaldehyde was added dropwise over one hour and below 50° C. Agitation was continued for one hour at room temperature to drive the reaction to completion. Then 300 g of water and 44 g of 20% HCl were added to the solution, which was agitated. Extraction with 500 g of 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 158.6 g of 5-(1-hydroxy-5-methoxypentyl)-2-norbornene. The yield was 75.4%.

Workup

  1. waitAgitation was continued for one hour at room temperature
  2. customthe reaction to completion
  3. extractionExtraction with 500 g of hexane
  4. customgave the organic layer, which
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuum
  9. customThe oily matter thus obtained
  10. distillationwas distilled in vacuum

Sources & evidence

ORD record
ord-13c6f83bf0f74ca2aa476057f187cee0
Source dataset
uspto-grants-2003_09
Patent number
US06624335B2

Reaction notes

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