Benzyl Bromide → 3-(Benzyloxy)-4-tert-butylphenyl tert-butyl carbonate

HRID 1350881Notes

Reaction equation

[C:1](=[O:19])([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[C:10]([OH:18])[CH:9]=1)[O:2][C:3]([CH3:6])([CH3:5])[CH3:4].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CC(C)=O>[C:1](=[O:19])([O:2][C:3]([CH3:6])([CH3:5])[CH3:4])[O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[C:10]([O:18][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:9]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To an acetone (100 mL) solution of tert-butyl 4-tert-butyl-3-hydroxyphenyl carbonate (J. Org. Chem. 2001, 66, 3435) (5.5 g, 20.7 mmol) were added potassium carbonate (8.6 g, 63 mmol) and benzyl bromide (3.0 ml, 25.0 mmol). The stirred mixture was refluxed at 65° C. for 4 hours. The precipitate was filtered off and washed with acetone. The filtrate was concentrated under reduced pressure to give a residue, which was applied to a silica gel chromatography column and eluted with ethyl acetate/hexane= 1/30 to furnish 7.1 g (96% yield) of the title compound as a colorless oil.

Workup

filtrationThe precipitate was filtered off
washwashed with acetone
concentrationThe filtrate was concentrated under reduced pressure
customto give a residue, which
washeluted with ethyl acetate/hexane= 1/30

Sources & evidence

ORD record: ord-e2ae9fce1f734accbb687dc4d8c6531f
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214824B2

Reaction notes

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