4-Hydroxybenzoic Acid → HCID 53969391, compound

HRID 864611Notes

Reaction equation

HRID 864611 reaction equation
S(C1C=CC(C)=CC=1)(O[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15])(=O)=O.OC1C=CC(C(O)=O)=CC=1.[Cl:33][C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][C:42]=1[OH:43])[C:37]([OH:39])=[O:38].[OH-].[K+]>C(O)C>[Cl:33][C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][C:42]=1[O:43][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:6]=[CH2:5])[C:37]([OH:39])=[O:38]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic Acid2×HCID 14797Potassium Hydroxide2×HCID 198603-Chloro-4-hydroxybenzoic acidHCID 11141895HCID 11141895, compound

Product 1

HCID 53969391HCID 53969391, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10-Undecen-1-yl Tosylate (compound I-7) was separately reacted with 4-hydroxybenzoic acid and 3-chloro-4-hydroxy-benzoic acid to synthesize the compounds I-18 and I-19. The synthesis of compound I-18 was described below as an example. 1.75 g (0.0312 mole) KOH, 0.05 g KI and 100 ml of 90% ethanol were mixed and refluxed. To the mixture 2.15 g (0.0156 mole) 4-hydroxybenzoic acid was added dropwise, and refluxed for one hour. 4.433 g (0.013 mole) compound I-7 was added slowly and refluxed for 10 hours. 10% KOH was then added and refluxed again for two hours. Ethanol was removed from the mixture which was then extracted with ethyl ether. The collected ethyl ether layer was dried over anhydrous MgSO4, filtered and concentrated to obtained solid product. The resulting solid product was recrystallized from ethanol. Yield: I-18: 40.6%; I-19: 36.4%. 1H-NMR:

Workup

  1. customto synthesize the compounds
  2. customThe synthesis of compound I-18
  3. temperaturerefluxed
  4. temperaturerefluxed for one hour
  5. temperaturerefluxed for 10 hours
  6. temperaturerefluxed again for two hours
  7. customEthanol was removed from the mixture which
  8. extractionwas then extracted with ethyl ether
  9. dry with materialThe collected ethyl ether layer was dried over anhydrous MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customto obtained solid product
  13. customThe resulting solid product was recrystallized from ethanol

Sources & evidence

ORD record
ord-90230dfae7a241ddbe8fffe2b399769e
Source dataset
uspto-grants-1996_10
Patent number
US05563230

Reaction notes

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