Ethanol → HCID 15027733, compound

HRID 1073231Notes

Reaction equation

HRID 1073231 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, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution containing 2.00g (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 0.75g 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
  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
  9. customThis material was 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-c2356ad02f4444d6aa1b5dc582842c2d
Source dataset
uspto-grants-1990_11
Patent number
US04968710

Reaction notes

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