4-tert-Butylphenol → HCID 14743498, compound

HRID 2166078Notes

Reaction equation

HRID 2166078 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[OH-].[CH2:15]([N+](C)(C)C)[C:16]1[CH:21]=CC=[CH:18][CH:17]=1.ClC(C)(C)C#C>ClCCl.O>[CH3:15][C:16]([O:11][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=1)([CH3:21])[C:17]#[CH:18]

Participants

7

Reactant 4

HCID 73934-tert-ButylphenolHCID 14798Sodium HydroxideHCID 66854Benzyltrimethylammonium hydroxideHCID 706791-Butyne, 3-chloro-3-methyl-

Product 1

HCID 14743498HCID 14743498, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-t-Butylphenol (10 g) and sodium hydroxide (3.99 g) were added to a stirred mixture of water (60 ml) and dichloromethane (60 ml) followed by benzyltrimethylammonium hydroxide (40% solution in methanol, 150 ml) and 3-chloro-3-methyl-butyne (13.65 g). After stirring at ambient temperature for 11 days, the layers were separated and the aqueous layer extracted with chloroform. The combined organic extracts were concentrated in vacuo and the residue dissolved in diethyl ether. The solution was washed with water, 10% sodium hydroxide solution, then brine, and dried over magnesium sulphate. Removal of drying agent and solvent gave 3-methyl-3-(4-t-butylphenoxy)-but-1-yne as a yellow oil (13.35 g).

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer extracted with chloroform
  3. concentrationThe combined organic extracts were concentrated in vacuo
  4. dissolutionthe residue dissolved in diethyl ether
  5. washThe solution was washed with water, 10% sodium hydroxide solution
  6. dry with materialbrine, and dried over magnesium sulphate
  7. customRemoval
  8. customof drying agent and solvent

Sources & evidence

ORD record
ord-a4384858ceaf48dca17d28341ff11ae4
Source dataset
uspto-grants-1990_07
Patent number
US04943582

Reaction notes

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