4-Hydroxybenzaldehyde → HCID 135714966, compound

HRID 1608548Notes

Reaction equation

HRID 1608548 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH2:10]([NH2:28])[CH2:11][CH2:12][CH2:13][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][CH3:27].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[N:28][CH2:10][CH2:11][CH2:12][CH2:13][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][CH3:27])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 6101p-Toluenesulfonic acidHCID 15793Octadecylamine

Product 1

HCID 135714966HCID 135714966, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, p-hydroxybenzaldehyde (99.6 g), n-octadecylamine (200.0 g) and p-toluenesulfonic acid (13.4 g) were added to toluene (1200 ml) and the mixture was refluxed with heating and simultaneously the azeotropic water was removed. After about 2 hours, the reaction mixture was cooled to room temperature to precipitate a crystal, which was filtered off under reduced pressure. This crystal was recrystallized from isopropanol to obtain the desired product (207.9 g). Yield 75%; m.p. 101° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating
  3. customsimultaneously the azeotropic water was removed
  4. customto precipitate a crystal, which
  5. filtrationwas filtered off under reduced pressure
  6. customThis crystal was recrystallized from isopropanol

Sources & evidence

ORD record
ord-5423c71bfb704af98b2598776ff98507
Source dataset
uspto-grants-1995_03
Patent number
US05395815

Reaction notes

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