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Sodium Hydroxide → HCID 15453776, compound

HRID 1108610
Notes
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Reaction equation

HRID 1108610 reaction equation
[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][O:5][CH:6]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:7]1[CH:12]=[CH:11][C:10]([C:13]([O:15]C)=[O:14])=[CH:9][CH:8]=1.[OH-].[Na+]>CO.Cl>[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][O:5][CH:6]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:7]1[CH:12]=[CH:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22320094HCID 22320094, compound

Product 1

HCID 15453776HCID 15453776, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

0.53 g(1.69 mmol) of methyl α-(2-dimethylaminoethoxy)-α-phenyl-p-toluate) was dissolved in 10 ml of methanol. 2.54 ml of a 1N sodium hydroxide aqueous solution was added thereto and the mixture was refluxed under heating for 1 hour. After the reaction mixture was cooled, 2.54 ml of IN hydrochloric acid was added thereto and the mixture was concentrated to dryness. A mixture of chloroform and methanol (5:1 (v/v)) was added to the residue, and the resulting mixture was stirred for a while, then filtered with Celite. The solvent was distilled off and the residue was triturated with diethyl ether. The resulting precipitate was collected by filtration to obtain 0.44 g (1.47 mmol) of α-(2-dimethylaminoethoxy)-α-phenyl-p-toluic acid as pale yellow brown powder. ##STR11## Its spectroscopic data are as follows: 1H-NMR (CDCl1) δ (ppm) 2.62 (6H, s), 3.00 (2H, m), 3.59 (1H, m), 3.82 (1H, m), 5.37 (1H, s), 7.21~7.36 (7H, m), 7.77 (2H, d, J=8.4 Hz).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 1 hour
  3. temperatureAfter the reaction mixture was cooled
  4. concentrationthe mixture was concentrated to dryness
  5. additionA mixture of chloroform and methanol (5:1 (v/v))
  6. additionwas added to the residue
  7. filtrationfiltered with Celite
  8. distillationThe solvent was distilled off
  9. customthe residue was triturated with diethyl ether
  10. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-cb47a84262d243ae919973dc22363e84
Source dataset
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06069149

Reaction notes

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