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Potassium Carbonate → 2-(4-benzyloxyphenoxy)propionic acid N-cyano-N-methylamide

HRID 235548
Notes
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Reaction equation

HRID 235548 reaction equation
[C:1]([N:3]([CH3:9])[C:4](=[O:8])[CH:5](Br)[CH3:6])#[N:2].C1(C(C2[C:23]([CH2:24][O:25][CH2:26][C:27]3[C:32](C4C(=CC=C(O)C=4)O)=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:22][CH:21]=[CH:20][CH:19]=2)=CC(=CC=1)O)O.C(=O)([O-])[O-:42].[K+].[K+]>CN(C)C=O>[C:1]([N:3]([CH3:9])[C:4](=[O:8])[CH:5]([O:42][C:21]1[CH:20]=[CH:19][C:24]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:23][CH:22]=1)[CH3:6])#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 537447922-Bromopropionic acid N-cyano-N-methylamideHCID 1317110222-[2-[[2-(2,5-Dihydroxyphenyl)phenyl]methoxymethyl]phenyl]benzene-1,4-diol

Product 1

HCID 545263512-(4-benzyloxyphenoxy)propionic acid N-cyano-N-methylamideYield 63%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

With efficient stirring, 19.1 g (0.1 mole) of 2-bromopropionic acid N-cyano-N-methylamide are added dropwise to a solution of 20.0 g (0.1 mole) of hydroquinone monobenzyl ether and 16.5 g (0.12 mole) of potassium carbonate in 200 ml of dimethylformamide. After the slightly exothermic reaction has subsided, the reaction mixture is heated for 3 hours to 40° C. The precipitated salts are then removed by filtration and the filtrate is concentrated by evaporation. The residue is dissolved in ether and the ether solution is extracted with dilute sodium hydroxide solution. The organic phase is dried over sodium sulfate, the solvent is evaporated off and the residue is distilled in vacuo, affording 19.5 g (63% of theory) of 2-(4-benzyloxyphenoxy)propionic acid N-cyano-N-methylamide with a melting point of 56°-58° C.

Workup

  1. customAfter the slightly exothermic reaction
  2. temperaturethe reaction mixture is heated for 3 hours to 40° C
  3. customThe precipitated salts are then removed by filtration
  4. concentrationthe filtrate is concentrated by evaporation
  5. dissolutionThe residue is dissolved in ether
  6. extractionthe ether solution is extracted with dilute sodium hydroxide solution
  7. dry with materialThe organic phase is dried over sodium sulfate
  8. customthe solvent is evaporated off
  9. distillationthe residue is distilled in vacuo

Sources & evidence

ORD record
ord-65d2d740e7b04bf0a9c2c6717e3e2219
Source dataset
uspto-grants-1987_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04640703

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes