Hydrochloric Acid → HCID 57221723, compound

HRID 1584525Notes

Reaction equation

HRID 1584525 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].[C:16]1(=O)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]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:16]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH:17]=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 10400Cycloheptanone

Product 1

HCID 57221723HCID 57221723, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture consisting of 82.5 g (0.40 mol) of 2,4-di-tert-butylphenol and 22.5 g (0.20 mol) of cycloheptanone is melted together and is then saturated, with stirring, with hydrochloric acid gas at 35-40° C. After 22 hours, the reaction mixture is again saturated with hydrochloric acid gas and then stirred for 17 hours. Subsequently, the 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=99:1 and the pure fractions are crystallised from ethanol, giving 5.4 g (9%) of 2,4-di-tert-butyl-6-cyclohepten-1-yl-phenol, m.p. 78-80° C. (compound (105), 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=99:1
  5. customthe pure fractions are crystallised from ethanol

Sources & evidence

ORD record
ord-76bbcb6151f441d6bdce05abec302180
Source dataset
uspto-grants-1999_08
Patent number
US05932642

Reaction notes

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