Benzyl Bromide → 1-Allyl-2-(benzyloxy)-3-tert-butylbenzene

HRID 2115922Notes

Reaction equation

HRID 2115922 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([CH3:13])([CH3:12])[CH3:11])[C:5]=1[OH:14])[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(C)(C)C>[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([CH3:13])([CH3:12])[CH3:11])[C:5]=1[O:14][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5206412-Allyl-6-t-butylphenol

Product 1

HCID 689642861-Allyl-2-(benzyloxy)-3-tert-butylbenzeneYield 88%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6386tert-ButanolSolvent

Procedure

Treatment of 2-allyl-6-tert-butylphenol (12.5 g, 0.066 mol) with potassium carbonate (27.24 g, 0.197 mol), benzyl bromide (11.80 g, 0.069 mol), and tetrabutylammonium iodide (2.43 g, 6.57 mmol) generally according to the procedure described for Intermediate 1 provided 16.2 g (88%) of 1-allyl-2-(benzyloxy)-3-tert-butylbenzene as a colorless oil. Anal. calcd. for C20H240: C, 85.67; H, 8.63. Found: C, 86.27; H, 8.77.

Sources & evidence

ORD record
ord-d316fbcda5f94e3ab44cd3ecbd6b34ca
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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