Hydrochloric Acid → HCID 15599100, compound

HRID 986806Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH3:20])[CH:13]=2)[CH:8]=[C:7]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:6]=1[OH:25])([CH3:4])([CH3:3])[CH3:2].[C:26]1(=[O:32])[O:31][C:29](=[O:30])[CH2:28][CH2:27]1.[OH-].[Na+].Cl>O>[C:1]([C:5]1[CH:10]=[C:9]([N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH3:20])[CH:13]=2)[C:26]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:32])[CH:8]=[C:7]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:6]=1[OH:25])([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 5 g (0.015 mole) of 2,6-di-tertiarybutyl-4-(3'-ethoxyanilino)phenol and 1.5 g (0.015 mole) of succinic anhydride was heated under a nitrogen atmosphere at 140° C. for two hours. The reaction was cooled to room temperature and the resulting glass was diluted with water. The addition of 100 ml of 10% sodium hydroxide failed to give a solution so the mixture was acidified with 10% hydrochloric acid. The resulting solid was collected and then recrystallized first from a mixture of ethanol and water and then from a mixture of diethyl ether and hexane to give 2.6 g of tan solid 3-[N-(3,5-di-tertiary-butyl-4-hydroxyphenyl)-N-(3-ethoxyphenyl)carbamoyl]propionic acid, m.p. 128°-130° C. Analysis: Calculated for C26H35NO5 : % C, 70.7; % H, 8.0; % N, 3.2; Found: % C, 70.5; % H, 7.8; % N, 3.4.

Workup

temperatureThe reaction was cooled to room temperature
customto give a solution so the mixture
customThe resulting solid was collected
customrecrystallized first from a mixture of ethanol and water
additionfrom a mixture of diethyl ether and hexane

Sources & evidence

ORD record: ord-053584c6d7664523815cc69fdfbba74c
Source dataset: uspto-grants-1987_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04716178

Reaction notes

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