Dicyclohexylcarbodiimide → HCID 21497740, compound

HRID 1730380Notes

Reaction equation

HRID 1730380 reaction equation
[C:1]([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](O)=[O:9])([CH3:4])([CH3:3])[CH3:2].[C:19]([C:23]1[CH:24]=[C:25]([CH:32]=[C:33]([C:36]([CH3:39])([CH3:38])[CH3:37])[C:34]=1[OH:35])[C:26]([O:28][CH2:29][CH2:30][NH2:31])=[O:27])([CH3:22])([CH3:21])[CH3:20].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[C:19]([C:23]1[CH:24]=[C:25]([CH:32]=[C:33]([C:36]([CH3:39])([CH3:38])[CH3:37])[C:34]=1[OH:35])[C:26]([O:28][CH2:29][CH2:30][NH:31][C:8](=[O:9])[C:7]1[CH:11]=[C:12]([C:15]([CH3:16])([CH3:17])[CH3:18])[C:13]([OH:14])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=1)=[O:27])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 713941812-Aminoethyl 3,5-di-tert-butyl-4-hydroxybenzoate

Product 1

HCID 21497740HCID 21497740, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 25 grams (0.1 mole) of 3,5-di-t-butyl-4-hydroxybenzoic acid and 29.3 grams (0.1 mole) of N-(3,5-di-t-butyl-4'hydroxybenzoyloxyethyl)amine in 100 milliliters of drytetrahydrofuran was added dropwise a solution of 20.6 grams (0.1 mole) of dicyclohexylcarbodiimide in 75 milliliters of dry tetrahydrofuran. The mixture was stirred for several hours and the white solid (dicyclohexyl urea) was filtered off and discarded. Evaporation of the filtrate gave a product which was recrystallized from 1:1 benzene-hexane to give N-(3',5'di-t-butyl-4'-hydroxybenzoyloxyethyl)-3,5-di-t-butyl-4-hydroxybenzamide; melting point 185°-187° C. When tested by the procedure of Example 2, the sample containing this compound lasted 1,000 hours, about 3.3 times as long as the control.

Workup

  1. filtrationthe white solid (dicyclohexyl urea) was filtered off
  2. customEvaporation of the filtrate
  3. customgave a product which
  4. customwas recrystallized from 1:1 benzene-hexane

Sources & evidence

ORD record
ord-27e2feff51ea4ab9b2fa509c1dab9f06
Source dataset
uspto-grants-1976_11
Patent number
US03992434

Reaction notes

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