Acetic Acid → HCID 20482486, compound

HRID 1389669Notes

Reaction equation

HRID 1389669 reaction equation
[O:1]=[C:2]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=1.[BH4-].[Na+].C(O)C.C(O)(=O)C>O>[OH:1][CH:2]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 20482520HCID 20482520, compound

Product 1

HCID 20482486HCID 20482486, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 10 g. of ethyl 4-(6-oxohexadecylamino)benzoate and 2.8 g. of sodium borohydride in 250 ml. of ethanol is stirred at ambient temperature for 3 hours, acidified with glacial acetic acid, and poured into water. The solid is collected by filtration, dried, and recrystallized from hexane to yield the product as a white solid. Alkaline hydrolysis of this ester by the method of Example 10 affords 4-(6-hydroxyhexadecylamino)benzoic acid.

Workup

  1. additionA suspension of 10 g
  2. filtrationThe solid is collected by filtration
  3. customdried
  4. customrecrystallized from hexane

Sources & evidence

ORD record
ord-dbf52a1a37624a4cb50cf8d600269d14
Source dataset
uspto-grants-1981_01
Patent number
US04245097

Reaction notes

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