Pyridine → HCID 20259843, compound

HRID 1583697Notes

Reaction equation

HRID 1583697 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([S:16][CH2:17][CH2:18][OH:19])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:26]([C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([C:40]([CH3:43])([CH3:42])[CH3:41])[C:38]=1[OH:39])[C:33](Cl)=[O:34])([CH3:29])([CH3:28])[CH3:27]>C1(C)C=CC=CC=1>[C:40]([C:37]1[CH:36]=[C:32]([CH:31]=[C:30]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:38]=1[OH:39])[C:33]([O:19][CH2:18][CH2:17][S:16][C:7]1[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]([OH:11])=[C:9]([C:12]([CH3:13])([CH3:15])[CH3:14])[CH:8]=1)=[O:34])([CH3:43])([CH3:42])[CH3:41]

Participants

5

Reactant 3

HCID 1049PyridineHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chlorideHCID 140118152,6-Di-tert-butyl-4-[(2-hydroxyethyl)sulfanyl]phenol

Product 1

HCID 20259843HCID 20259843, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 9.8 g of 2-(3,5-di-tert-butyl-4-hydroxyphenylthio) ethanol and 3.1 g of pyridine in 40 ml of toluene was added at 15°-20° C. over five minutes to a solution of 9.4 g of 3,5-di-tert-butyl-4-hydroxybenzoyl chloride in 50 ml of toluene. The reaction mixture was stirred at room temperature for 15 hours and then the resultant precipitate of triethylamine hydrochloride was removed by filtration. The solvent was removed in vacuo and the residue was recrystalized from n-heptane to give 15 g (84%) of a white solid, mp 136°-139° C.

Workup

  1. customthe resultant precipitate of triethylamine hydrochloride was removed by filtration
  2. customThe solvent was removed in vacuo
  3. customthe residue was recrystalized from n-heptane

Sources & evidence

ORD record
ord-2b3d901ade354fcca4e3e062ea1c1aaa
Source dataset
uspto-grants-1985_11
Patent number
US04552926

Reaction notes

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