3-(3',5'-Di-tert-butyl-4'-hydroxyphenyl)propionic acid → HCID 21488283, compound

HRID 1974010Notes

Reaction equation

HRID 1974010 reaction equation
O[CH:2]1[CH2:9][CH2:8][CH:7]([OH:10])[CH:6]2[N:11]([CH3:12])[CH:3]1[CH2:4][CH2:5]2.[C:13]([C:17]1[CH:18]=[C:19]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH:20]=[C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:22]=1[OH:23])([CH3:16])([CH3:15])[CH3:14]>C1(C)C(C)=CC=CC=1.CCOCC.[Ti]>[C:13]([C:17]1[CH:18]=[C:19]([CH2:28][CH2:29][C:30]([O:32][CH:3]2[CH2:4][CH2:5][CH:6]3[N:11]([CH3:12])[CH:2]2[CH2:9][CH2:8][CH:7]3[O:10][C:30](=[O:31])[CH2:29][CH2:28][C:19]2[CH:20]=[C:21]([C:24]([CH3:25])([CH3:27])[CH3:26])[C:22]([OH:23])=[C:17]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:18]=2)=[O:31])[CH:20]=[C:21]([C:24]([CH3:25])([CH3:26])[CH3:27])[C:22]=1[OH:23])([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 2

HCID 883893-(3',5'-Di-tert-butyl-4'-hydroxyphenyl)propionic acidHCID 214882869-Methyl-9-azabicyclo[4.2.1]nonane-2,5-diol

Product 1

HCID 21488283HCID 21488283, compoundYield 56.6%

Reagents, catalysts & solvents 3

HCID 23963TitaniumCatalystHCID 3283Diethyl EtherSolventHCID 7237O-XyleneSolvent

Procedure

In a nitrogen atmosphere a stirred mixture of the diol mixture 2,6-dihydroxy-9-methyl-9-azabicyclo[3.3.1]nonane and 2,5-dihydroxy-9-methyl-9-azabicyclo[4.2.1]nonane (4.28 g., 0.025 mole), 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid (15.3 g, 0.055 mole) and 0.7 ml of titanium tetraisopripylate in 100 ml of xylene was heated under reflux in a flask equipped with a Dean-Stark trap for 14 hours. The xylene was evaporated under reduced pressure and the residue thus obtained was dissolved in ether. The ether solution was washed with 5% aqueous sodium hydroxide and then water. The dried (Na2SO4) solution was evaporated under reduced pressure to give an oily residue which was crystallized from petroleum ether. Recrystallization from methanol gave 9.8 g (56.6%) of the title ester, m.p. 107°-109°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux in a flask
  3. customequipped with a Dean-Stark trap for 14 hours
  4. customThe xylene was evaporated under reduced pressure
  5. customthe residue thus obtained
  6. washThe ether solution was washed with 5% aqueous sodium hydroxide
  7. dry with materialThe dried (Na2SO4) solution
  8. customwas evaporated under reduced pressure
  9. customto give an oily residue which
  10. customwas crystallized from petroleum ether
  11. customRecrystallization from methanol

Sources & evidence

ORD record
ord-e0f4042f88fe4b3d81609b12ab42ffdb
Source dataset
uspto-grants-1976_12
Patent number
US04000113

Reaction notes

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