Potassium Iodide → Ethyl 2-[4-(2-acetaminoethyl)-phenoxy]-n-hexanoate

HRID 127978Notes

Reaction equation

HRID 127978 reaction equation
[NH:1]([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[C:2]([CH3:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].Br[CH:21]([CH2:27][CH2:28][CH2:29][CH3:30])[C:22]([O:24][CH2:25][CH3:26])=[O:23].[I-].[K+]>CC(=O)CC>[NH:1]([CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH:21]([CH2:27][CH2:28][CH2:29][CH3:30])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:11][CH:12]=1)[C:2]([CH3:4])=[O:3]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 79072Ethyl 2-bromohexanoateHCID 121051N-Acetyltyramine

Product 1

HCID 23471007Ethyl 2-[4-(2-acetaminoethyl)-phenoxy]-n-hexanoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 17.92 g. (0.1 mol) 4-(2-acetamino-ethyl)-phenol, 17.3 g. (0.125 mol) pulverized potassium carbonate and 150 ml. butan-2-one is stirred for 2 hours at reflux temperature, then 27.9 g. (0.125 mol) ethyl 2-bromohexanoate and a spatula tip of potassium iodide are added thereto and the reaction mixture kept at reflux temperature for a further 28 hours. The reaction mixture is then filtered with suction and the filtrate evaporated in a vacuum. The residue is taken up in diethyl ether and the ethereal phase is extracted with 2 N hydrochloric acid, water, 0.5 N aqueous sodium hydroxide solution and again with water, dried over anhydrous sodium sulphate and evaporated to give 32.1 g. (quantitative yield) ethyl 2-[4-(2-acetaminoethyl)-phenoxy]-n-hexanoate in the form of a colorless oil with a refractive index nD20 =1.5010.

Workup

  1. additionA mixture of 17.92 g
  2. temperatureat reflux temperature
  3. temperatureat reflux temperature for a further 28 hours
  4. filtrationThe reaction mixture is then filtered with suction
  5. customthe filtrate evaporated in a vacuum
  6. extractionthe ethereal phase is extracted with 2 N hydrochloric acid, water, 0.5 N aqueous sodium hydroxide solution and again with water
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated
  9. customto give 32.1 g

Sources & evidence

ORD record
ord-c67c2d22b85d49fdb645d6a6873f889f
Source dataset
uspto-grants-1981_03
Patent number
US04258058

Reaction notes

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