Diethyl Ether → m-Diethyl-aminophenol

HRID 375669Notes

Reaction equation

HRID 375669 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C([N-:11][CH2:12][CH3:13])C.[Li+].[CH2:15](OCC)[CH3:16]>>[CH2:4]([C:3]1([OH:8])[CH:2]=[CH:7][CH:6]=[C:13]([CH2:15][CH3:16])[CH:12]1[NH2:11])[CH3:5]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 72442-BromophenolHCID 11137085Lithium diethylamide

Product 1

HCID 69344032m-Diethyl-aminophenolYield 15%

Procedure

Amer. Chem. Soc., 74 (1952), 3027-29, discloses that the treatment of o-bromophenol with twice the molar amount of lithium diethylamide in boiling diethyl ether gives rise to m-diethyl-aminophenol. However, the process described there is completely unsuitable for an industrial synthesis, since m-diethylaminophenol is formed only in a yield of 15%.

Sources & evidence

ORD record
ord-83a89c98682c4f9eb7fc4b16ecc6391c
Source dataset
uspto-grants-1996_01
Patent number
US05486609

Reaction notes

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