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

HRID 1282933Notes

Reaction equation

HRID 1282933 reaction equation
[CH2:1](O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:16]=1[OH:25])([CH3:14])([CH3:13])[CH3:12].O>C(O)=O.C(O)(=O)C>[C:21]([C:17]1[CH:18]=[C:19]([CH2:1][CH:2]=[CH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:20]=[C:15]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:16]=1[OH:25])([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 3083-Phenylprop-2-En-1-OlHCID 962WaterHCID 314052,6-Di-tert-butylphenol

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 284Formic AcidSolvent

Procedure

Cinnamyl alcohol (134 g.) was added to a suspension of 2,6-di-t-butylphenol (206 g.) in 88% aqueous formic acid (470 ml.) and glacial acetic acid (200 ml.), and the mixture was refluxed for 1.5 hours. Warm water (2000 ml.) was added and the oily layer which formed on top of the mixture was collected. The oil was distilled and gave a fraction (179 g.), b.p. 190°-200°C. at 0.5 mm Hg. The oil crystallized upon treatment with Skelly F (a mixture of petroleum hydrocarbons boiling between 30°-60°C.) to give glistening, colorless needles, m.p. 93°C. (Found: C, 85.7; H, 9.20. Calc. for C23H30O: C. 85.7; H, 9.38). The nuclear magnetic resonance (nmr) spectrum of this compound at 100 MHz in deuterated chloroform (CDCl3) exhibited absorbances as follows: a singlet (9 protons) at δ 1.41; a singlet (9 protons) at δ 1.45; a singlet (2 protons) at δ 3.48; a singlet (1 proton) at δ 5.07; a multiplet (2 protons) at δ 6.18-6.58; and a multiplet (7 protons) at δ 6.96-7.46.

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. customthe oily layer which formed on top of the mixture
  3. customwas collected
  4. distillationThe oil was distilled
  5. customgave a fraction (179 g.), b.p. 190°-200°C. at 0.5 mm Hg
  6. customThe oil crystallized upon treatment with Skelly F (
  7. additiona mixture of petroleum hydrocarbons boiling between 30°-60°C.)
  8. customto give

Sources & evidence

ORD record
ord-3ab72459e740486d87d133b88a03d1a9
Source dataset
uspto-grants-1976_08
Patent number
US03973040

Reaction notes

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