Diethyl Ether → N,N-diethyl-4-hydroxybenzamide

HRID 361700Notes

Reaction equation

HRID 361700 reaction equation
C([Li])CCC.[CH2:6]([NH:8][CH2:9][CH3:10])[CH3:7].[OH:11][C:12]1[CH:22]=[CH:21][C:15]([C:16]([O:18]CC)=O)=[CH:14][CH:13]=1.C(OCC)C>CCCCCC.O1CCCC1>[OH:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([N:8]([CH2:9][CH3:10])[CH2:6][CH3:7])=[O:18])=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8021DiethylamineHCID 8434EthylparabenHCID 178418339Butyllithium

Product 1

HCID 504154N,N-diethyl-4-hydroxybenzamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of n-butyl lithium in hexane (1.6M, 22.87 ml) was added to a solution of diethylamine (3.74 ml) in dry tetrahydrofuran (100 ml), at ambient temperature and under an atmosphere of argon. The reaction mixture was stirred for 15 minutes. Ethyl 4-hydroxybenzoate (5 g) was then added and the reaction mixture stirred for 16 hours. Diethyl ether was added to the reaction mixture and the mixture was washed with water, dried (MgSO4) and evaporated. The residue was purified by flash column chromatography on silica gel (Merck Art No. 9385) using a 1:3 (v/v) mixture of ethyl acetate/hexane as eluent to give 4-hydroxy-N,N-diethyl benzamide as a solid (1.17 g), m.p. 122.5° C.; NMR ([CD3 ]2SO): 1.1-1.15(6H,t), 3.2-3.4(4H,m), 6.75-6.85(2H,d), 7.15-7.25(2H,d), and 9.7(1H,s); m/z 194(M+H).

Workup

  1. stirringthe reaction mixture stirred for 16 hours
  2. washthe mixture was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by flash column chromatography on silica gel (Merck Art No. 9385)
  6. additiona 1:3 (v/v) mixture of ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-632b7deaeb454ff0a016bd7dde929327
Source dataset
uspto-grants-1999_02
Patent number
US05866611

Reaction notes

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