Ethanol → HCID 15027733, compound

HRID 974104Notes

Reaction equation

HRID 974104 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:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]Br)#[N:18].[OH-].[Na+].C(O)C>O>[C:12]([C:7]1[CH:8]=[C:9]([S:11][CH2:22][C:21]2[CH:24]=[CH:25][CH:26]=[C:19]([C:17]#[N:18])[CH:20]=2)[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 97249Benzonitrile, 3-(bromomethyl)-

Product 1

HCID 15027733HCID 15027733, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution containing 2.009 (8.39 mmole) of 2,6-di-t-butyl-4-mercaptophenol, 1.65 g (8.39 mmole) of m-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 then extracted with diethyl ether. The ether extract was washed with water, dried with magnesium sulfate and evaporated to give the crude product This material was purified by silica gel chromatography eluting with 1% ethyl acetate in hexane, followed by four recrystallizations from hexane to give 0.75 g of 2,6-di-t-butyl-4-[(3-cyanophenyl)methylthio]phenol as white needles, m.p. 61°-63° C. Analysis: Calculated for C22H27NOS: %C, 74 7%; %H, 7.7; %N, 4.0; Found: %C. 74.5; %H, 8.0; %N, 3.8.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 hours The reaction mixture
  3. extractionwas then extracted with diethyl ether
  4. extractionThe ether extract
  5. washwas washed with water
  6. dry with materialdried with magnesium sulfate
  7. customevaporated
  8. customto give the crude product This material
  9. customwas purified by silica gel chromatography
  10. washeluting with 1% ethyl acetate in hexane
  11. customfollowed by four recrystallizations from hexane

Sources & evidence

ORD record
ord-6c950cf5a19d4b13bcac6dbd3fc2356c
Source dataset
uspto-grants-1991_11
Patent number
US05066822

Reaction notes

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