Water → HCID 86600358, compound

HRID 2373763Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[C:9]([NH2:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].[C:17]([O-:20])(=[O:19])[CH3:18].[Na+].[C:22](OCCBr)(=O)[CH3:23].O>C(O)C>[C:17]([O:20][N:11]([CH2:22][CH3:23])[C:9]1[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]([OH:16])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=1)(=[O:19])[CH3:18]

Participants

Conditions

Temperature: 65 °C

Procedure

1 g (4.5 mmol) of 2,6-di-t-butyl-4-aminophenol (intermediate 10.2) and 0.65 g of sodium acetate (7.9 mmol) are put into suspension in 1 ml of ethanol. Then bromoethyl acetate (0.94 g, 5.65 mmol) is added to the medium and the reaction medium is heated at 65° C. for 2 hours. The reaction mixture is poured into 20 ml of ice-cooled water and the reaction product is extracted with dichloromethane (3 times 15 ml). The organic phases are dried and the solvent is evaporated off under reduced pressure. The residue is passed over silica gel in dichloromethane. A colourless oil is obtained constituted by a mixture of 2 compounds: the product of mono- and di-substitution. The mixture of these 2 compounds is used without further purification in the following stage.

Workup

extractionthe reaction product is extracted with dichloromethane (3 times 15 ml)
customThe organic phases are dried
customthe solvent is evaporated off under reduced pressure
customA colourless oil is obtained
additionconstituted by a mixture of 2 compounds
additionThe mixture of these 2 compounds
customis used without further purification in the following stage

Sources & evidence

ORD record: ord-127a2539f4bf4739ab5985281a967b66
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459558B2

Reaction notes

Loading…