Hydrochloric Acid → 3-Hydroxy-4-(1-oxo-2-methylbutyl)phenyl 4-(4'-octyloxyphenyl)benzoate

HRID 345738Notes

Reaction equation

HRID 345738 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([OH:14])[CH:5]=[CH:6][C:7]=1[C:8](=[O:13])[CH:9]([CH3:12])[CH2:10][CH3:11].[CH2:15]([O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=2)=[CH:26][CH:25]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].Cl.C(Cl)(Cl)Cl>N1C=CC=CC=1.C(Cl)Cl.C(OCC)C>[CH2:15]([O:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]2[CH:38]=[CH:37][C:33]([C:34]([O:14][C:4]3[CH:5]=[CH:6][C:7]([C:8](=[O:13])[CH:9]([CH3:12])[CH2:10][CH3:11])=[C:2]([OH:1])[CH:3]=3)=[O:35])=[CH:32][CH:31]=2)=[CH:28][CH:29]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 110784734-(4-Octyloxyphenyl)benzoyl chlorideHCID 147163011-(2,4-Dihydroxyphenyl)-2-methyl-1-butanone2×

Product 1

HCID 147163033-Hydroxy-4-(1-oxo-2-methylbutyl)phenyl 4-(4'-octyloxyphenyl)benzoateYield 7.8%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

0.5 g of 3-hydroxy-4-(1-oxo-2-methylbutyl)phenol prepared by the process described in (1) was dissolved in 15 ml of anhydrous pyridine, to which added was a solution of 0.7 g of 4-(4'-octyloxyphenyl)benzoic acid chloride dissolved in 20 ml of anhydrous methylene chloride dropwisely over a period of about one hour under stirring. The reaction mixture was stirred at the room temperature for additional 40 hours to proceed the reaction. Then, the reaction mixture was added to 300 ml of dilute hydrochloric acid solution. After adding 50 ml of chloroform and 50 ml of ethyl ether, followed by shaking, the organic phase was separated from the aqueous phase. The organic phase was rinsed with a dilute hydrochloric acid solution for two times, rinsed with an aqueous solution of NaHCO3 for one time, and then rinsed with a 3% aqueous solution of NaCl for three times. Anhydrous Na2SO4 was added to the organic phase to dry the same. After removing the drying agent by filtration, the solvent was distilled off to obtain a crude product which was refined through silica gel column chromatography while using chlorofrom as the eluent. The thus obtained product was recrystallized from a mixed solvent composed of 10 parts by volume of chloroform and 90 parts by volume of n-hexane. As a result, 0.08 g of 3-hydroxy-4-(1-oxo-2-methylbutyl)phenyl 4-(4'-octyloxyphenyl)benzoate was obtained.

Workup

  1. additionadded
  2. stirringThe reaction mixture was stirred at the room temperature for additional 40 hours
  3. customthe reaction
  4. stirringby shaking
  5. customthe organic phase was separated from the aqueous phase
  6. washThe organic phase was rinsed with a dilute hydrochloric acid solution for two times
  7. washrinsed with an aqueous solution of NaHCO3 for one time
  8. washrinsed with a 3% aqueous solution of NaCl for three times
  9. additionAnhydrous Na2SO4 was added to the organic phase
  10. customto dry the same
  11. customAfter removing the drying agent
  12. filtrationby filtration
  13. distillationthe solvent was distilled off
  14. customto obtain a crude product which
  15. customThe thus obtained product was recrystallized from a mixed solvent

Sources & evidence

ORD record
ord-c89aba52f1c347a78a7b220149829e93
Source dataset
uspto-grants-1991_10
Patent number
US05059345

Reaction notes

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