Hydrochloric Acid → HCID 86639744, compound

HRID 1643233Notes

Reaction equation

HRID 1643233 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([SH:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].[C:17]([OH:24])(=[O:23])[CH2:18][CH2:19][C:20]([CH3:22])=O.Cl>C(OC(C)C)(C)C>[C:1]([C:5]1[CH:10]=[C:9]([S:11][C:20]([S:11][C:9]2[CH:8]=[C:7]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:6]([OH:16])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=2)([CH3:22])[CH2:19][CH2:18][C:17]([OH:24])=[O:23])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11579Levulinic AcidHCID 703702,6-Di-tert-butyl-4-mercaptophenol

Product 1

HCID 86639744HCID 86639744, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

To a solution of 2,6-di-t-butyl-4-mercaptophenol (4.77 g, 20.0 mmol) in isopropyl ether (50 mL) was added levulinic acid (1.16 g, 10.0 mmol) and a catalytic amount of concentrated hydrochloric acid. The mixture was heated under reflux over 10 days. The solvent was distilled off from the reaction mixture, and the resulting residue was purified by a flash column chromatography (filler: manufactured by Kanto Kagaku, K.K., 60Nmesh40-100, developing solvent:n-hexane/ethyl acetate (volume ratio)=5/1 to 2/1) to give 4,4-bis(3,5-di-t-butyl-4-hydroxyphenylthio)pentanoic acid (yield 935 mg and 16%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux over 10 days
  3. distillationThe solvent was distilled off from the reaction mixture
  4. customthe resulting residue was purified by a flash column chromatography (filler: manufactured by Kanto Kagaku, K.K., 60Nmesh40-100, developing solvent:n-hexane/ethyl acetate (volume ratio)=5/1 to 2/1)

Sources & evidence

ORD record
ord-ed460955065540228f211a2a0fdaa79e
Source dataset
uspto-grants-2012_02
Patent number
US08119686B2

Reaction notes

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