Toluene → 2-Stearamidoethyl 3,4-di-tert-butyl-4-hydroxybenzoate

HRID 1659908Notes

Reaction equation

HRID 1659908 reaction equation
C([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8]([OH:10])=[O:9])(C)(C)C.[C:19]1([CH3:25])[CH:24]=CC=C[CH:20]=1.S(Cl)(Cl)=O.O[CH2:31][CH2:32][NH:33][C:34](=[O:52])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51]>N1C=CC=CC=1>[C:15]([CH:12]1[C:13]([C:19]([CH3:25])([CH3:24])[CH3:20])([OH:14])[CH:5]=[CH:6][C:7]([C:8]([O:10][CH2:31][CH2:32][NH:33][C:34](=[O:52])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])=[O:9])=[CH:11]1)([CH3:16])([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 24386Thionyl ChlorideHCID 27902N-Stearoylethanolamine

Product 1

HCID 705659952-Stearamidoethyl 3,4-di-tert-butyl-4-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 25 g (0.1 mole) 3,5-di-tert-butyl-4-hydroxybenzoic acid, 50 ml toluene and 8.5 ml thionyl chloride was refluxed for 3 hours. The excess thionyl chloride and the toluene were removed on a rotary evaporator. The acid chloride was dissolved in 50 ml toluene and was added to a mixture of 29.4 g (0.09 mole) N-(2-hydroxyethyl)stearamide, 20 ml toluene and 15 ml pyridine. The mixture was refluxed for two hours. The reaction mixture was then cooled, quenched with water, washed with dilute hydrochloric acid and with water. The toluene was removed by distillation, and the residue was crystallized from hexane. The title compound thus obtained melted at 56°-58° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customThe excess thionyl chloride and the toluene were removed on a rotary evaporator
  3. dissolutionThe acid chloride was dissolved in 50 ml toluene
  4. temperatureThe mixture was refluxed for two hours
  5. temperatureThe reaction mixture was then cooled
  6. customquenched with water
  7. washwashed with dilute hydrochloric acid and with water
  8. customThe toluene was removed by distillation
  9. customthe residue was crystallized from hexane

Sources & evidence

ORD record
ord-e04349d6adcb43a9bd7514c7e121c661
Source dataset
uspto-grants-1981_12
Patent number
US04305868

Reaction notes

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