Water → 2,6-Di-tert-butyl-4-(prop-2-en-1-yl)phenol

HRID 1902904Notes

Reaction equation

HRID 1902904 reaction equation
[OH-].[Na+].O.[C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:9]=1[OH:18])([CH3:7])([CH3:6])[CH3:5].[CH2:19](Br)[CH:20]=[CH2:21]>C1(C)C=CC=CC=1>[C:14]([C:10]1[CH:11]=[C:12]([CH2:21][CH:20]=[CH2:19])[CH:13]=[C:8]([C:4]([CH3:7])([CH3:6])[CH3:5])[C:9]=1[OH:18])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 14798Sodium Hydroxide2×HCID 314052,6-Di-tert-butylphenol2×

Product 1

HCID 109228432,6-Di-tert-butyl-4-(prop-2-en-1-yl)phenol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
25 °C

Procedure

A 1 liter, 3 neck flask equipped with a mechanical stirrer, thermometer, nitrogen inlet, dropping funnel and condenser was charged with 40 grams (1.0 mole) of sodium hydroxide and 50 ml. of H2O. The NaOH was dissolved with stirring and the solution was cooled to 25° C. and then 100 ml. of toluene, 2.06 grams (0.01 moles) 2,6-di-t-butyl phenol and 6.25 grams (≈0.006 moles) of S-X1 polystyrene quaternary phosphonium resin catalyst was charged into the reaction vessel. The dropping funnel was charged with a solution prepared from 49.44 grams (0.264 mole) of 2,6-di-t-butyl phenol, 32.0 grams (0.264 mole) of allyl bromide and 100 ml. of toluene. This solution was then added dropwise over a 40 minute period to the reaction vessel which had been heated to 50°-60° C. as stirring took place under a nitrogen blanket. After 3 hours of reaction time at 72° C. gas chromatographic analysis indicated that 50% of the starting materials had reacted to form 2,6-di-t-butyl-4-allyl phenol.

Workup

  1. customA 1 liter, 3 neck flask equipped with a mechanical stirrer
  2. customthermometer, nitrogen inlet, dropping
  3. additionThe dropping funnel was charged with a solution
  4. additionThis solution was then added dropwise over a 40 minute period to the reaction vessel which
  5. temperaturehad been heated to 50°-60° C.
  6. stirringas stirring
  7. customAfter 3 hours of reaction time at 72° C. gas chromatographic analysis
  8. customhad reacted

Sources & evidence

ORD record
ord-eb7d89650d554281825f0a8590016742
Source dataset
uspto-grants-1982_12
Patent number
US04366331

Reaction notes

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