Phenol → HCID 19737031, compound

HRID 258216Notes

Reaction equation

HRID 258216 reaction equation
[C:1]([C:6]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:9]=[CH:8][C:7]=1[OH:16])([CH2:4][CH3:5])([CH3:3])[CH3:2].[OH-].[Na+].[C:19]1([OH:25])C=CC=CC=1.C(Cl)(Cl)Cl.S(=O)(=O)(O)O>C(O)C.O>[C:1]([C:6]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:9]=[C:8]([CH:19]=[O:25])[C:7]=1[OH:16])([CH2:4][CH3:5])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 996PhenolHCID 1118Sulfuric AcidHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 15173853HCID 15173853, compound

Product 1

HCID 19737031HCID 19737031, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

2-t-amyl-4-t-butylphenol (53 g, 0.24 mole) is dissolved in 150 ml absolute ethanol in a 1 L round bottom flask equipped with a water-cooled condenser. Sodium hydroxide (96 g, 2.4 moles) is dissolved in 100 ml water, and the hot solution is added to the solution of the phenol. Chloroform (57 g, 0.48 mole) is added in 1 ml portions over a 45-minute period. The resulting yellow-brown mixture is stirred 1 hour as it cools to ambient temperature. The mixture is diluted into 500 ml of 1M sulfuric acid and extracted with 200 ml hexanes. The organic layer is isolated in a separatory funnel and dried over anhydrous magnesium sulfate. The mixture is filtered and rotoevaporated to a thick syrup. A typical yield for this reaction is 30%. The product is used without further purification.

Workup

  1. temperaturecooled condenser
  2. customcools to ambient temperature
  3. extractionextracted with 200 ml hexanes
  4. customThe organic layer is isolated in a separatory funnel
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe mixture is filtered
  7. customA typical yield for this reaction
  8. customThe product is used without further purification

Sources & evidence

ORD record
ord-824f082b12774114b37a96452042050a
Source dataset
uspto-grants-1993_11
Patent number
US05266283

Reaction notes

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