Acetone → Benzoic acid, p-(2-(diethylamino)ethoxy)-, methyl ester

HRID 729930Notes

Reaction equation

HRID 729930 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:20][CH2:21][NH:22][CH2:23][CH3:24].[I-].[K+].[CH3:27][C:28](C)=O>>[CH2:21]([N:22]([CH2:27][CH3:28])[CH2:23][CH2:24][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[CH3:20]

Participants

6

Reactant 5

HCID 180AcetoneHCID 4875Potassium IodideHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 130140362-Chloro-N-ethylethan-1-amine--hydrogen chloride (1/1)

Product 1

HCID 19002Benzoic acid, p-(2-(diethylamino)ethoxy)-, methyl ester

Procedure

A mixture of methyl 4-hydroxybenzoate (15.21 g, 0.1 mol), anhydrous potassium carbonate (34.55 g, 0.25 mol), 2-chloro-N,N-diethylamine hydrochloride (25.81 g, 0.15 mol), potassium iodide (0.166 g, g, 0.001 mol) and acetone (75 ml) was heated under reflux for 10-9 h. On cooling, the solid was removed by filtration and the solvent was evaporated. The residue was dissolved in toluene (75 ml) and the solution was washed with sodium hydroxide solution (2% w/v, 30 ml) and deionized water (2×30 ml). Removal of the solvent afforded methyl 4-(2-diethylaminoethyloxy)benzoate as an oil which was dissolved in ethanol (50 ml) and added to a solution of sodium hydroxide (10.0 g, 0.2 mol) in water (50 ml). The mixture was heated under reflux for 2 h. The ethanol was removed in vacuo and the aqueous solution was acidified with hydrochloric acid (12N) at 5-6° C. The solid was collected, triturated with water (previously cooled to 5-6° C.), filtered and dried at 55-60° C. in vacuo and recrystallized from water to give 10. 4-(2-Diethylaminoethoxy)benzoic acid hydrochloride (10). M.p. 170-172° [lit.[22], m.p. 171-174°]. Yield: 73%. 1H NMR (D2O): 1.17-1.20 (t, 6H, 2×CH3), 3.13-3.24 (m, 4H, 2×CH2), 3.47-3.48 (t, 2H, OCH2CH2N), 4.26-4.28 (t, 2H, OCH2CH2N), 6.89-6.91 (d, 2H, aryl H), 7.80-7.82 (d, 2H, aryl H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10-9 h
  3. temperatureOn cooling
  4. customthe solid was removed by filtration
  5. customthe solvent was evaporated
  6. dissolutionThe residue was dissolved in toluene (75 ml)
  7. washthe solution was washed with sodium hydroxide solution (2% w/v, 30 ml) and deionized water (2×30 ml)
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-116bea7a088a43bcaacaeb627ab575f4
Source dataset
uspto-grants-2009_09
Patent number
US07582655B2

Reaction notes

Loading…