Ethanol → HCID 15027735, compound

HRID 974105Notes

Reaction equation

HRID 974105 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]([C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21]Br)#[N:18].[OH-].[Na+].C(O)C>O>[C:12]([C:7]1[CH:8]=[C:9]([S:11][CH2:21][C:20]2[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=2[C:17]#[N:18])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:16])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 895992-(Bromomethyl)benzonitrile

Product 1

HCID 15027735HCID 15027735, compoundYield 18.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2.00 g (8.39 mmole) of 2,6-di-t-butyl-4-mercaptophenol, 1.65 g (8.39 mmole) of o-cyanobenzyl bromide, 5 ml of 1.68N sodium hydroxide and 75 ml of ethanol was heated at reflux for 48 hours. The reaction mixture was poured into water and was extracted with diethyl ether. The ether extract was washed with water, dried with magnesium sulfate and evaporated to give the crude product as an oil. The oil was purified by silica gel chromatography, eluting with a mixture of ethyl acetate and hexane, followed by recrystallization from hexane to give 0.56 g of white 2,6-di-t-butyl-4-[(2-cyanophenyl) methylthio]phenol, m.p. 79°-82° C. Analysis: Calculated for C22H27NOS: %C, 74.7; %H, 7.7; %N, 4.0; Found: %C, 74.6; %H, 7.9; %N 3.6.

Workup

  1. temperatureat reflux for 48 hours
  2. extractionwas extracted with diethyl ether
  3. extractionThe ether extract
  4. washwas washed with water
  5. dry with materialdried with magnesium sulfate
  6. customevaporated
  7. customto give the crude product as an oil
  8. customThe oil was purified by silica gel chromatography
  9. washeluting with a mixture of ethyl acetate and hexane
  10. customfollowed by recrystallization from hexane

Sources & evidence

ORD record
ord-c6acf8581aa94020bef339b8aa22323e
Source dataset
uspto-grants-1991_11
Patent number
US05066822

Reaction notes

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