Sulfuric Acid → HCID 12773506, compound

HRID 648633Notes

Reaction equation

HRID 648633 reaction equation
S(=O)(=O)(O)O.[N:6]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:18](O)[CH3:19])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C(OC(=O)C1C=CC(CC#N)=CC=1)C>C(OCC)(=O)C>[N:6]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:18]=[CH2:19])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 11989373ethyl 4-(cyanomethyl)benzoate2×HCID 12707338HCID 12707338, compound

Product 1

HCID 12773506HCID 12773506, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

An amount of 1.6 ml of conc. sulfuric acid was added in small drops to a mixture of 2 gm (9.74 m mol) of 1-(2-piperidino-phenyl)-ethanol and 4 gm (21.1 m mol) of 4-cyanomethylbenzoic acid ethyl ester under stirring and cooling with ice by keeping the internal temperature at 35° to 40° C. Subsequently, the mixture was heated for 2.5 hours in a bath of 80° C., a further 2 gm (10.5 m mol) of 4-cyanomethyl benzoic acid ethyl ester and 0.8 ml of conc. sulfuric acid were added, and heating was continued for one hour at 80° C. and for three hours at 100° C. After that time no starting alcohol could be detected in a thin layer chromatogram. After cooling to 20° C. the mixture was layered with ethyl acetate, and under stirring and cooling ice water was added. After extraction several times with ethyl acetate, the organic extract was dried over sodium sulfate, filtered, and evaporated in vacuo. The evaporation residue was purified by column chromatography on silica gel (toluene/acetone=10:1). From the pre-fractions 0.5 gm of 2-piperidino-styrol was isolated.

Workup

  1. temperaturecooling with ice
  2. customat 35° to 40° C
  3. temperatureheating
  4. temperatureAfter cooling to 20° C. the mixture
  5. stirringunder stirring
  6. additionwas added
  7. extractionAfter extraction several times with ethyl acetate
  8. extractionthe organic extract
  9. dry with materialwas dried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated in vacuo
  12. customThe evaporation residue was purified by column chromatography on silica gel (toluene/acetone=10:1)

Sources & evidence

ORD record
ord-c75d97d249e840ecbd7a7f12b329bf3b
Source dataset
uspto-grants-1988_04
Patent number
US04735959

Reaction notes

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