Ethyl bromoacetate → Ethyl [3-(benzyloxy)-4-tert-butylphenoxy]acetate

HRID 1350883Notes

Reaction equation

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

Participants

Reactant 3

HCID 7748Ethyl bromoacetate

HCID 11430Potassium Carbonate

HCID 210974743-(Benzyloxy)-4-tert-butylphenol

Product 1

HCID 58640422Ethyl [3-(benzyloxy)-4-tert-butylphenoxy]acetateYield 85.2%

Procedure

3-(Benzyloxy)-4-tert-butylphenol (4.9 g, 19.2 mmol), potassium carbonate (8.0 g, 57.6 mmol) and ethyl bromoacetate (2.6 ml, 23.0 mmol) were treated in the same procedure described in Example 13(d). The crude residue was applied to a silica gel chromatography column and eluted with a volume mixture of hexane and ethyl acetate (29/1 to 19/1) to furnish 5.6 g (85% yield) of the title compound as a colorless oil.

Workup

washeluted with a volume mixture of hexane and ethyl acetate (29/1 to 19/1)

Sources & evidence

ORD record: ord-c14fae49147e453885f9d5b703067996
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214824B2

Reaction notes

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