2,4-Di-tert-butylphenol → HCID 50888872, compound

HRID 1030448Notes

Reaction equation

[OH-].[Na+].[CH2:3](Br)[CH:4]=[CH2:5].[C:7]([C:11]1[CH:16]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:14]=[CH:13][C:12]=1[OH:21])([CH3:10])([CH3:9])[CH3:8]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O>[C:7]([C:11]1[CH:16]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:14]=[CH:13][C:12]=1[O:21][CH2:5][CH:4]=[CH2:3])([CH3:10])([CH3:9])[CH3:8]

Participants

Conditions

Temperature: 50 °C

Procedure

Sodium hydroxide pellets (20 g, 0.5 moles), water (25 g), toluene (50 ml) and tetrabutylammonium hydrogen sulphate (1 g) are added in succession into a reactor. They are heated to 50° C. with stirring and under nitrogen and a toluene solution (50 ml) of allyl bromide (16.5 g, 0.134 moles) and of 2,4-di-tert-butylphenol (25 g, 0.12 moles) is added over 45 minutes. The temperature rises progressively to 68° C. The materials are left at this temperature for 3 hours. Cooling is applied, 50 ml of water and 50 ml of toluene are added and the phases are separated. The toluene phase is washed with water and dried over sodium sulphate and the solvent is evaporated off to give an orange-coloured oil which is purified on a bed of silica gel 60 (eluent: heptane). 2,4-Di-tert-butylallyloxybenzene is obtained as a colourless liquid (23 g, yield =78 %).

Workup

customrises progressively to 68° C
temperatureCooling
customthe phases are separated
washThe toluene phase is washed with water
dry with materialdried over sodium sulphate
customthe solvent is evaporated off
customto give an orange-coloured oil which
customis purified on a bed of silica gel 60 (eluent: heptane)

Sources & evidence

ORD record: ord-eee69f14f5e44d51bc0bdb93601ca808
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05106611

Reaction notes

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