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Acetic Acid → 4-({[4-(Tridecyloxy)phenyl]methyl}amino)benzoic acid

HRID 2052490
Notes
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Reaction equation

HRID 2052490 reaction equation
[CH2:1]([O:14][C:15]1[CH:33]=[CH:32][C:18]([CH2:19][NH:20][C:21]2[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[OH-].[K+].C(O)C.O.C(O)(=O)C>O>[CH2:1]([O:14][C:15]1[CH:33]=[CH:32][C:18]([CH2:19][NH:20][C:21]2[CH:31]=[CH:30][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 13079677Ethyl 4-({[4-(tridecyloxy)phenyl]methyl}amino)benzoateHCID 19096565Water ethanol

Product 1

HCID 130796764-({[4-(Tridecyloxy)phenyl]methyl}amino)benzoic acid

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent
2×

Procedure

A mixture of 7.0 g. of ethyl p-[(p-tridecyloxybenzyl)amino]benzoate (prepared as described in Example 22), 7.0 g. of potassium hydroxide and 150 ml. of ethanol-water (9:1) is refluxed for 3.5 hours. The solution is acidified while hot, diluted with water, filtered and the solid washed with water to give white crystals, m.p. 110°-113° C. and 145°-150° C. The solid is heated with 200 ml. of glacial acetic acid and the solution chilled and filtered to give crystals, m.p. 110°-112° C. and 155°-160° C. The filtrate is diluted with water to give white crystals (pure by TLC) m.p. 108°-122° C. and 150°-155° C. The first crop of crystals is slurried in 75 ml. of acetone, filtered and the filtrate chilled and filtered. The filtrate is diluted with water to give white crystals (pure by TLC). The two crops pure by TLC are combined, dried in vacuo to give white crystals, m.p. 110°-112° C. and 155°-160° C.

Workup

  1. additionA mixture of 7.0 g
  2. filtrationfiltered
  3. washthe solid washed with water
  4. customto give white crystals, m.p. 110°-113° C. and 145°-150° C
  5. temperatureThe solid is heated with 200 ml
  6. filtrationfiltered
  7. customto give crystals, m.p. 110°-112° C. and 155°-160° C
  8. customto give white crystals (pure by TLC) m.p. 108°-122° C. and 150°-155° C
  9. filtrationof acetone, filtered
  10. temperaturethe filtrate chilled
  11. filtrationfiltered
  12. additionThe filtrate is diluted with water
  13. customto give white crystals (pure by TLC)
  14. customdried in vacuo
  15. customto give white crystals, m.p. 110°-112° C. and 155°-160° C.

Sources & evidence

ORD record
ord-5aa545051b2944a0a48e69acc6b0d386
Source dataset
uspto-grants-1980_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04185115

Reaction notes

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