Acetic Acid → HCID 12944319, compound

HRID 1606740Notes

Reaction equation

HRID 1606740 reaction equation
[CH2:1]([C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][CH2:12][CH:13]2[C:18]([NH2:20])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=[O:23])C>>[C:1]([C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][CH2:12][CH:13]2[C:18]([NH2:20])=[O:19])(=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 20310111HCID 20310111, compound

Product 1

HCID 12944319HCID 12944319, compound

Procedure

To 100 ml. of acetic acid is added 6.6 g. of 5-benzyl-1,2,3,4-tetrahydro-1-naphthamide and, under cooling with ice, 3.4 g. of chromic anhydride is added. The mixture is stirred well. After stirring overnight, the reaction mixture is poured over 500 g. of ice and the resultant crystals are collected by filtration. This is subjected to column chromtography on silica gel using chloroform as the eluent and the eluate is recrystallized from cyclohexane. The procedure gives 5-benzoyl-1,2,3,4-tetrahydro-1-naphthamide, melting point: 145.5°-147.5°C.

Workup

  1. stirringAfter stirring overnight
  2. additionthe reaction mixture is poured over 500 g
  3. filtrationof ice and the resultant crystals are collected by filtration
  4. customthe eluate is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-a529adabdb7046d9b8da740e28dfe40e
Source dataset
uspto-grants-1976_04
Patent number
US03953500

Reaction notes

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