Hydrochloric Acid → HCID 19737033, compound

HRID 258213Notes

Reaction equation

HRID 258213 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:19])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[C:22]1([OH:28])C=CC=CC=1.C(Cl)(Cl)Cl.Cl>C(O)C.O>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:13])[CH3:12])[CH:8]=[C:7]([CH:22]=[O:28])[C:6]=1[OH:19])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 996PhenolHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 605573Phenol, 2-(1,1-dimethylethyl)-4-(1,1,3,3-tetramethylbutyl)-

Product 1

HCID 19737033HCID 19737033, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

2-t-butyl-4-t-octylphenol (140 g, 0.53 mole) was dissolved in 420 ml of absolute ethanol in a 3 L round bottom flask equipped with a water-cooled condenser. Sodium hydroxide (213 g, 5.3 moles) was dissolved in 200 ml water and added while still hot to the solution of phenol. Chloroform (127 g, 1.06 mole) was added in 2 to 3 ml portions over a 1 hour period. The resulting yellow-brown mixture was stirred for 1 hour while it cooled to ambient temperature. The mixture was diluted into 500 ml of 5M hydrochloric acid. The organic layer was isolated in a separatory funnel and dried over anhydrous magnesium sulfate. The mixture was filtered and rotoevaporated to a thick syrup to yield 26% crude product with an IR spectrum having the characteristic aldehyde carbonyl stretching frequency. The product was used without further purification.

Workup

  1. temperaturecooled condenser
  2. customThe organic layer was isolated in a separatory funnel
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-65d6bea4e2d849a89eee1ca1732bf0e7
Source dataset
uspto-grants-1993_11
Patent number
US05266283

Reaction notes

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