3-(3',5'-Di-tert-butyl-4'-hydroxyphenyl)propionic acid → HCID 13135952, compound

HRID 2290445Notes

Reaction equation

HRID 2290445 reaction equation
[N:1]1([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:18]([C:22]1[CH:23]=[C:24]([CH2:33][CH2:34][C:35](O)=[O:36])[CH:25]=[C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:27]=1[OH:28])([CH3:21])([CH3:20])[CH3:19]>C1(C)C(C)=CC=CC=1>[C:29]([C:26]1[CH:25]=[C:24]([CH2:33][CH2:34][C:35]([N:4]2[CH2:3][CH2:2][N:1]([C:7]3[CH:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:16][CH:17]=3)[CH2:6][CH2:5]2)=[O:36])[CH:23]=[C:22]([C:18]([CH3:20])([CH3:19])[CH3:21])[C:27]=1[OH:28])([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 2

HCID 883893-(3',5'-Di-tert-butyl-4'-hydroxyphenyl)propionic acidHCID 2761178Ethyl 4-(piperazin-1-yl)benzoate

Product 1

HCID 13135952HCID 13135952, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 23.4 g. (0.1 mole) ethyl 4-(piperazin-1-yl)-benzoate (base), 600 ml. xylene and 27.8 g. (0.1 mole) 3-(3,5-di-tert.-butyl-4-hydroxyphenyl)-propionic acid is boiled under a water separator for 28 hours, then evaporated to dryness in a vacuum and the residue is taken up with diethyl ether. For the removal of unreacted ethyl 4-(piperazin-1-yl)-benzoate, the ether solution is extracted with 1N hydrochloric acid, washed with water and aqueous sodium bicarbonate solution, dried with anhydrous sodium sulphate and mixed with hydrogen chloride-containing diethyl ether, whereby the hydrochloride precipitates out. This is washed with diethyl ether and recrystallised from ethanol to give 32.0 g. (60% of theory) of the desired product as colourless crystals; m.p. 196°-198° C.

Workup

  1. additionA mixture of 23.4 g
  2. customfor 28 hours
  3. customevaporated to dryness in a vacuum
  4. customFor the removal of unreacted ethyl 4-(piperazin-1-yl)-benzoate
  5. extractionthe ether solution is extracted with 1N hydrochloric acid
  6. washwashed with water and aqueous sodium bicarbonate solution
  7. dry with materialdried with anhydrous sodium sulphate
  8. additionmixed with hydrogen chloride-
  9. additioncontaining diethyl ether, whereby the hydrochloride
  10. customprecipitates out
  11. washThis is washed with diethyl ether
  12. customrecrystallised from ethanol
  13. customto give 32.0 g

Sources & evidence

ORD record
ord-a6fc459b3f8b4b51888569d3958a07a4
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

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