1-Butanol → 3-Butoxy-4-tert-butylphenyl tert-butyl carbonate

HRID 1350872Notes

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].[CH2:20](O)[CH2:21][CH2:22][CH3:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=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][CH2:20][CH2:21][CH2:22][CH3:23])[CH:9]=1

Participants

Reactant 4

HCID 2631-Butanol

HCID 11776Triphenylphosphine

HCID 220568ethyl N-ethoxycarbonyliminocarbamate

HCID 15482845Tert-butyl 4-tert-butyl-3-hydroxyphenyl carbonate

Product 1

HCID 210974823-Butoxy-4-tert-butylphenyl tert-butyl carbonateYield 66%

Procedure

tert-Butyl 4-tert-butyl-3-hydroxyphenyl carbonate (1.5 g, 5.6 mmol), n-butanol (0.5 mL, 5.4 mmol), triphenylphosphine (1.3 g, 5.0 mmol) and diethyl azodicarboxylate (DEAD) (0.78 mL, 5.0 mmol) were treated in the same procedure described in Example 31(a). The crude residue was applied to a silica gel chromatography column and eluted with a volume mixture of hexane and ethyl acetate (19/1 to 9/1) to furnish 964 mg (66% yield) of the title compound as a colorless oil.

Workup

washeluted with a volume mixture of hexane and ethyl acetate (19/1 to 9/1)

Sources & evidence

ORD record: ord-a3ed0b6bf2c94409b49065e29afcfabc
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214824B2

Reaction notes

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