Acetic Acid → 4-[(Cyclooctylmethyl)amino]benzoic acid

HRID 2419352Notes

Reaction equation

HRID 2419352 reaction equation
[CH:1]1([CH:9]=O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1.C(O)(=O)C>[Zn].C1C=CC=CC=1>[CH:1]1([CH2:9][NH:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9784-Aminobenzoic AcidHCID 81190Cyclooctanecarbaldehyde

Product 1

HCID 203156154-[(Cyclooctylmethyl)amino]benzoic acid

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 241BenzeneSolvent

Procedure

Cyclooctane carboxaldehyde (14.72 g, 0.105 mole) was added dropwise to a stirred and refluxing mixture of 13.7 g (0.1 mole) p-aminobenzoic acid, 25 g zinc dust, 25 ml glacial acetic acid and 125 ml of benzene. Water which evolved was collected in a Dean-Stark trap as the reaction mass was refluxed overnight. Following the reflux period, the resulting product mass was filtered while still hot. Upon cooling the filtrate, crystals formed therein. The benzene was evaporated and the residue recrystallized from acetonitrile. The crude product weighed 18.77 g. It was decolorized and recrystallized from benzene. The resulting purified 4-[(cyclooctylmethyl)amino]benzoic acid product weighed 12.93 g. It had a melting point of 160°-162° C.

Workup

  1. temperaturerefluxing
  2. customWater which evolved was collected in a Dean-Stark trap as the reaction mass
  3. temperaturewas refluxed overnight
  4. filtrationthe resulting product mass was filtered while still hot
  5. temperatureUpon cooling the filtrate, crystals
  6. customformed
  7. customThe benzene was evaporated
  8. customthe residue recrystallized from acetonitrile
  9. customrecrystallized from benzene
  10. customThe resulting purified 4-[(cyclooctylmethyl)amino]benzoic acid product

Sources & evidence

ORD record
ord-7ba8eb41de204883a5d3a85144a0dcfd
Source dataset
uspto-grants-1978_08
Patent number
US04105791

Reaction notes

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