Diethyl Ether → Salicylamide

HRID 277310Notes

Reaction equation

HRID 277310 reaction equation
ClC1C=C(C(CCO)C[NH:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)C=CC=1Cl.CC[O:25]CC.[OH-].[Na+]>O1CCCC1.Cl.O>[OH:25][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]([NH2:11])=[O:19]

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 22137555N-[2-(3,4-Dichlorophenyl)-4-hydroxybutyl]benzamide

Product 1

HCID 5147Salicylamide

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-[2-(3,4-Dichlorophenyl)-4-hydroxybutyl]benzamide. A solution of the above ether (4.0 g) in tetrahydrofuran (20 mL) and 3 N hydrochloric acid (20 mL) was stirred for 2 hours. The reaction mixture was diluted with water, neutralized with 1 N sodium hydroxide, and extracted with dichloromethane. The organic extracts were dried, evaporated, and chromatographed, with dichloromethane:methanol (95:5) as eluent, to give the hydroxy benzamide compound as a viscous oil (2.9 g); NMR: 7.63 (m,2), 7.47 (m,1), 7.37 (m,3), 7.32 (d,1, J=2.1), 7.06 (dd,1, J=2.1, 8.3), 6.46 (m,1), 3.82 (m,1), 3.69 (m,1), 3.57-3.39 (m,2), 3.12 (m,1), 2.60 (m,1), 1.97 (m,1), 1.82 (m,1); MS: m/z=338(M+1).

Workup

  1. extractionextracted with dichloromethane
  2. customThe organic extracts were dried
  3. customevaporated
  4. customchromatographed, with dichloromethane:methanol (95:5) as eluent

Sources & evidence

ORD record
ord-f4d83c039de54870b839942196d7300d
Source dataset
uspto-grants-2002_03
Patent number
US06355695B1

Reaction notes

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