Water → HCID 21337830, compound

HRID 1937275Notes

Reaction equation

HRID 1937275 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:18](Br)[CH2:19][CH2:20][CH2:21][CH3:22].O>C(#N)C>[CH2:18]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([CH:11]2[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]2)[CH:9]=[CH:10][C:2]=1[OH:1])[CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 80571-BromopentaneHCID 22460221HCID 22460221, compound

Product 1

HCID 21337830HCID 21337830, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

13.60 g (70 mmols) of 2-hydroxy-5-(4-oxocyclohexyl)benzoic acid was suspended in 90 ml of acetonitrile. 10.66 g (70 mmols) 1,8-diazabicyclo[5.4.0]undec-7-ene(1,5-5) (DBU) was added dropwise at 20° C. over a period of 10 minutes, followed by 11.63 g (77 mmols) pentyl bromide over a further period of 10 minutes. The suspension was then stirred under reflux for 18 hours. After cooling the reaction mixture was poured into 300 ml of water and extracted three times with 150 ml of acetic ester. The combined organic phases were washed once with 200 ml 1N HCl, three times with 150 ml of water, dried over magnesium sulphate and filtered. Removal of the solvent gave the crude product which was purified by chromatography on silica gel, eluting with cyclohexane/acetic ester to give 2-hydroxy-5-(4-oxocyclohexyl)benzoic acid pentyl ester.

Workup

  1. temperatureunder reflux for 18 hours
  2. temperatureAfter cooling the reaction mixture
  3. extractionextracted three times with 150 ml of acetic ester
  4. washThe combined organic phases were washed once with 200 ml 1N HCl, three times with 150 ml of water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customRemoval of the solvent
  8. customgave the crude product which
  9. customwas purified by chromatography on silica gel
  10. washeluting with cyclohexane/acetic ester

Sources & evidence

ORD record
ord-63074e07a5954b8f9ee2d565a84e501e
Source dataset
uspto-grants-2002_05
Patent number
US06395351B1

Reaction notes

Loading…