Hydrochloric Acid → 4-(Hexadecylamino)benzoic acid

HRID 1659628Notes

Reaction equation

HRID 1659628 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[Cl-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC.Cl>C(O)C>[CH2:29]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 9784-Aminobenzoic AcidHCID 82131-BromohexadecaneHCID 14797Potassium HydroxideHCID 9890573Phosphonium, tributylhexadecyl-, chloride

Product 1

HCID 472634-(Hexadecylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

27.4 g (0.2 mol) of 4-aminobenzoic acid, 11.2 g of KOH, 64 g (0.21 mol) of 1-bromohexadecane and 4.64 g (10 mmol) of hexadecyltributylphosphonium chloride were suspended in 250 ml of ethanol (96%) and the reaction mixture was stirred for 12 hours at reflux temperature. While the solution was still hot, there were added, drop by drop, 80 ml of conc. HCl and the reaction mixture was left to cool down to ambient temperature. Thereupon the precipitated product was separated on a suction filter, washed with water and dried. After the crystallization of the crude product from benzene, there was obtained the 4-(n-hexadecylamino)-benzoic acid, m.p. 107°-107° C., complete m.p. 122°-126° C., which could be optionally converted into its sodium salt.

Workup

  1. temperatureat reflux temperature
  2. additionthere were added
  3. customThereupon the precipitated product was separated on a suction
  4. filtrationfilter
  5. washwashed with water
  6. customdried
  7. customAfter the crystallization of the crude product from benzene

Sources & evidence

ORD record
ord-753192602afc4e6bbffd5580619d74ca
Source dataset
uspto-grants-1981_12
Patent number
US04304929

Reaction notes

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