Hydrochloric Acid → HCID 21224649, compound

HRID 1584526Notes

Reaction equation

HRID 1584526 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17]1([CH3:25])[CH2:22][CH:21]([CH3:23])[CH2:20][C:19](=O)[CH2:18]1.Cl>CCCCCC>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([C:19]2[CH2:18][C:17]([CH3:25])([CH3:16])[CH2:22][CH:21]([CH3:23])[CH:20]=2)[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 73112,4-Di-tert-butylphenolHCID 133983,3,5-Trimethylcyclohexanone

Product 1

HCID 21224649HCID 21224649, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture consisting of 30.9 g (0.15 mol) of 2,4-di-tert-butylphenol and 10.5 g (0.075 mol) of 3,3,5-trimethylcyclohexanone is melted together and is then saturated, with stirring, with hydrochloric acid gas at 35° C. After 24 hours, the reaction mixture is again saturated with hydrochloric acid gas and is then stirred for 20 hours. Subsequently, the green reaction mixture is diluted with hexane and washed with water and sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated on a rotary evaporator. The residue is chromatographed over silica gel using the solvent system hexane/ethyl acetate=49:1, giving 10.6 g (43%) of 2,4-di-tert-butyl-6-(3,5,5-trimethylcyclohexen-1-yl)phenol as a thick yellowish oil (compound (106), Table 1).

Workup

  1. washwashed with water and sodium chloride solution
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. concentrationconcentrated on a rotary evaporator
  4. customThe residue is chromatographed over silica gel using the solvent system hexane/ethyl acetate=49:1

Sources & evidence

ORD record
ord-7c16b9d8ad114247a64311ae86a82c87
Source dataset
uspto-grants-1999_08
Patent number
US05932642

Reaction notes

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