Phenol → Di-tert-butyl ether

HRID 2186330Notes

Reaction equation

[C:1]1([OH:7])[CH:6]=CC=C[CH:2]=1.CNC(=NC)O[C:12]([CH3:15])([CH3:14])[CH3:13].[C:18](OCC)(=O)C.CCCCCC>>[C:12]([O:7][C:1]([CH3:2])([CH3:6])[CH3:18])([CH3:15])([CH3:14])[CH3:13]

Participants

Reactant 3

HCID 996Phenol

HCID 21226206Ethyl acetate hexane

HCID 23001675N,N'-dimethyl-O-t-butylisourea

Product 1

HCID 22541Di-tert-butyl etherYield 15%

Procedure

Following a procedure analogous to (3b), the phenol from (3a) (270 mg, 0.97 mmol) was reacted with N,N′-dimethyl-O-t-butylisourea. Silica gel chromatography (ethyl acetate-hexane, 20:80) gave the t-butyl ether (50.2 mg, 15%) as a 1:1 mixture of two isomers. MS found: (M+H)+=334.

Sources & evidence

ORD record: ord-536bd073ddca4d228083b1e88c75a837
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403632B1

Reaction notes

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