2,6-Di-tert-butyl-4-(3-phenylprop-2-en-1-yl)phenol → 2,6-Di-tert-butyl-4-(3-phenylpropyl)phenol

HRID 1282935Notes

Reaction equation

HRID 1282935 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH2:11][CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=[C:7]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:6]=1[OH:24])([CH3:4])([CH3:3])[CH3:2].[H][H]>O1CCCC1.[Pd]>[C:20]([C:7]1[CH:8]=[C:9]([CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:24])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 2

HCID 540633162,6-Di-tert-butyl-4-(3-phenylprop-2-en-1-yl)phenolHCID 178418361HCID 178418361, compound

Product 1

HCID 203607202,6-Di-tert-butyl-4-(3-phenylpropyl)phenolYield 82.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2,6-Di-t-butyl-4-cinnamylphenol (30 g., prepared as described in Example 2) was catalytically 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 was evaporated to an oil. Distillation of the oil gave the desired compound (25 g.) as an oil, b.p. 195°-200°C. at 10.5 mm. Hg. The nmr spectrum in CDCl3 at 100 MHz exhibited absorbances as follows: a singlet (9 protons) at δ 1.40, a singlet (9 protons) at δ 1.43, a multiplet (2 protons) at δ 1.75-2.10, a multiplet (4 protons) at δ 2.43-2.82, a singlet (1 proton) at δ 5.00, a singlet (2 protons) at δ 6.98, and a multiplet (5 protons) at δ 7.08-7.40.

Workup

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

Sources & evidence

ORD record
ord-17184bcdaab444d7a5686ec8e4371c1f
Source dataset
uspto-grants-1976_08
Patent number
US03973040

Reaction notes

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