Diethanolamine → HCID 21497741, compound

HRID 1730379Notes

Reaction equation

HRID 1730379 reaction equation
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].[C:8]([C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])[C:15](Cl)=[O:16])([CH3:11])([CH3:10])[CH3:9]>O1CCCC1.C1C=CC=CC=1>[OH:4][CH2:3][CH2:2][N:1]([CH2:5][CH2:6][O:7][C:15](=[O:16])[C:14]1[CH:18]=[C:19]([C:22]([CH3:23])([CH3:24])[CH3:25])[C:20]([OH:21])=[C:12]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:13]=1)[C:15](=[O:16])[C:14]1[CH:13]=[C:12]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:20]([OH:21])=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:18]=1

Participants

5

Reactant 2

HCID 8113DiethanolamineHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chloride

Product 1

HCID 21497741HCID 21497741, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cold (5° C.) solution of 3 moles of diethanolamine in tetrahydrofuran was added dropwise a solution of 3,5-di-t-butyl-4-hydroxybenzoyl chloride in benzene. The reaction mixture was stirred for about 1 hour, washed with water, separating the benzene layer from the aqueous layer. The benzene solution was evaporated to yieldan oil, which, after crystallization with aqueous ethanol, yielded a white solid. Small amounts of by-product compounds of Examples 1 and 3 were removed by fractional crystallization to yield N-hydroxyethyl-N-(3',5'-di-t-butyl-4'-hydroxybenzoyloxyethyl)-3,5-di-t-butyl-4-hydroxybenzamide; melting point 174°-178° C. When testedby the procedure of Example 2, the sample containing this compound lasted 1,200 hours, about 2.2 times as long as the control.

Workup

  1. washwashed with water
  2. customseparating the benzene layer from the aqueous layer
  3. customThe benzene solution was evaporated
  4. customafter crystallization with aqueous ethanol
  5. customyielded a white solid
  6. customSmall amounts of by-product compounds of Examples 1 and 3 were removed by fractional crystallization

Sources & evidence

ORD record
ord-782d84cb6d9f4b219a6f49bfaee1426c
Source dataset
uspto-grants-1976_11
Patent number
US03992434

Reaction notes

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