Triethylamine → 3-(3,5-Di-tert-butyl-4-hydroxyphenylthio)-n-butanal

HRID 65165Notes

Reaction equation

HRID 65165 reaction equation
[CH:1](=[O:5])/[CH:2]=[CH:3]/[CH3:4].[C:6]([C:10]1[CH:15]=[C:14]([SH:16])[CH:13]=[C:12]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:11]=1[OH:21])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:6]([C:10]1[CH:15]=[C:14]([S:16][CH:3]([CH3:4])[CH2:2][CH:1]=[O:5])[CH:13]=[C:12]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:11]=1[OH:21])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 447466Crotonaldehyde

Product 1

HCID 136435693-(3,5-Di-tert-butyl-4-hydroxyphenylthio)-n-butanal

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.12 Grams of crotonaldehyde (0.042 mole) are added dropwise over a 15 minute period at 17°-22° C. to a solution of 10.8 grams of 2,6-di-tert-butyl-4-mercaptophenol (0.044 moles) and 0.5 gram of triethylamine in 20 ml of toluene and allowed to react in a nitrogen atmosphere at room temperature for 30 minutes and then at 50°-55° C. for two hours. Analysis indicates that the reaction is substantially complete at this point. The product, isolated as a light yellow liquid, is obtained in nearly quantitative yield after stripping off volatiles at 40° to 50° C. at 0.15 mm. Hg.

Workup

  1. customto react in a nitrogen atmosphere at room temperature for 30 minutes
  2. customThe product, isolated as a light yellow liquid
  3. customis obtained in nearly quantitative yield
  4. customat 40° to 50° C.

Sources & evidence

ORD record
ord-9c76c6a2d05f4e7a816c9ee0a6329b5a
Source dataset
uspto-grants-1986_09
Patent number
US04612341

Reaction notes

Loading…