HCID 320686, compound → 2,4-Di-tert-butyl-6-(3-phenylpropyl)phenol

HRID 2082797Notes

Reaction equation

HRID 2082797 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([CH2:16][CH:17]=[CH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>O1CCCC1.[Pd]>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([CH2:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 320686HCID 320686, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 542140132,4-Di-tert-butyl-6-(3-phenylpropyl)phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4,6-Di-t-butyl-2-cinnamylphenol (11.0 g., prepared as described in Example 1) was hydrogenated at room temperature and pressure in tetrahydrofuran (100 ml.) in the presence of 5% palladium on charcoal. The reaction was allowed to proceed until uptake of hydrogen ceased. The mixture was filtered and the filtrate evaporated to an oil. Distillation of the oil gave the desired compound as a colorless oil, b.p. 186°-187° C. at 0.5 mm. Hg. The nmr spectrum at 100 MHz in CDCl3 exhibited absorbances as follows: a singlet (9 protons) at δ 1.30, a singlet (9 protons) at δ 1.43, a multiplet (2 protons) at δ 1.85-204, a multiplet (4 protons) at δ 2.50-2.80, a singlet (1 proton) at δ 4.58, a doublet (1 proton) at δ 6.99 (J = coupling constant = 2.0 Hz), and a multiplet (6 protons) at δ 7.13-7.36.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated to an oil
  4. distillationDistillation of the oil

Sources & evidence

ORD record
ord-e0cd4a82ebc9476cb4bf8ace9a4f0157
Source dataset
uspto-grants-1978_04
Patent number
US04082814

Reaction notes

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