Ethanol → HCID 2314306, compound

HRID 1073229Notes

Reaction equation

HRID 1073229 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][C:22]([CH2:23]Br)=[CH:21][CH:20]=1)#[N:18].[OH-].[Na+].C(O)C>O>[C:12]([C:7]1[CH:8]=[C:9]([S:11][CH2:23][C:22]2[CH:25]=[CH:26][C:19]([C:17]#[N:18])=[CH:20][CH:21]=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 869964-(Bromomethyl)benzonitrile

Product 1

HCID 2314306HCID 2314306, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2.00 g (8.39 mmole) of the known compound 2,6-di-t-butyl-4-mercaptophenol, 1.65 g (8.39 mmole) of p-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 recrystallizations from a mixture of ethyl acetate and hexane and from ethanol to give 1.1 g of 2,6-di-t-butyl-4-[(4-cyanophenyl)methylthio]phenol as white needles, m.p. 143°-145° C. Analysis: Calculated for C22H27NOS: %C, 74.7; %H, 7 7; %N, 4.0; Found: %C, 75.1; %H, 8.1; %N, 4.1.

Workup

  1. temperatureat reflux for 48 hours
  2. extractionwas then 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
  8. customThis material was purified by silica gel chromatography
  9. washeluting with 1% ethyl acetate in hexane
  10. customfollowed by recrystallizations from a mixture of ethyl acetate and hexane and from ethanol

Sources & evidence

ORD record
ord-eef9b683a4e642eda99661da4282eba4
Source dataset
uspto-grants-1990_11
Patent number
US04968710

Reaction notes

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