Benzene → methyl 3-[p-(epsilon-N-acetylaminocaproyl)phenyl]-propionate

HRID 1995147Notes

Reaction equation

HRID 1995147 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)(=[O:3])[CH3:2].S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].[C:21]1([CH:27](C)[C:28]([O:30][CH3:31])=[O:29])C=CC=CC=1.[CH:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(=S)=S>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([C:33]1[CH:38]=[CH:37][C:36]([CH2:21][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:35][CH:34]=1)=[O:12])(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 241BenzeneHCID 20056-Acetylaminocaproic acidHCID 24386Thionyl ChlorideHCID 569653Methyl alpha-methylbenzeneacetateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13050879methyl 3-[p-(epsilon-N-acetylaminocaproyl)phenyl]-propionate

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

Eight hundred milligrams of ε-N-acetylaminocaproyl chloride obtained by reacting ε-N-acetylaminocaproic acid with thionyl chloride in benzene was suspended in 20 ml of carbon disulfide. With vigorous stirring under ice cooling, 1.3 g of aluminum chloride was added. A solution of 550 mg of methyl phenylpropionate in 5 ml of carbon disulfide was added, and the mixture was stirred for 4 hours under reflux. After the reaction, the carbon disulfide layer was separated by decantation. A small amount of ice water was carefully added to the residue to decompose the excess of aluminum chloride. An aqueous solution of sodium hydroxide was added to the resulting aqueous solution to dissolve the resulting aluminum hydroxide. It was extracted three times with chloroform. The chloroform layer was washed with water and dried over anhydrous sodium sulfate. The chloroform was distilled off under reduced pressure to give 900 mg of a white oily substance. The product had the following NMR spectrum and identified as the title compound.

Workup

  1. stirringthe mixture was stirred for 4 hours
  2. temperatureunder reflux
  3. customAfter the reaction
  4. customthe carbon disulfide layer was separated by decantation
  5. additionA small amount of ice water was carefully added to the residue
  6. additionAn aqueous solution of sodium hydroxide was added to the resulting aqueous solution
  7. dissolutionto dissolve the resulting aluminum hydroxide
  8. extractionIt was extracted three times with chloroform
  9. washThe chloroform layer was washed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationThe chloroform was distilled off under reduced pressure
  12. customto give 900 mg of a white oily substance

Sources & evidence

ORD record
ord-2a22cca72ff349a8bbb49f2e0c0794eb
Source dataset
uspto-grants-1983_09
Patent number
US04402975

Reaction notes

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