Benzyl Bromide → HCID 67436496, compound

HRID 1663504Notes

Reaction equation

HRID 1663504 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)C>[CH2:21]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8]([OH:10])=[O:9])=[CH:13][CH:14]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27749582-(4-Aminophenoxy)-2-methylpropanoic acid

Product 1

HCID 67436496HCID 67436496, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.95 g (0.01 mole) of 4-aminophenoxyisobutyric acid, 25 ml of ethanol, 1.76 g (0.02 mole) of potassium carbonate and 1.2 ml (0.01 mole) of benzyl bromide was stirred and refluxed for 24 hours. Most of the ethanol was evaporated. The residue was dissolved in water, charcoaled, filtered, and acidified water acetic acid to give an oily material which by cooling turned into a solid with a melting point of 194-196° C. The structure (shown below as Formula EX1) was confirmed by NMR spectroscopy.

Workup

  1. temperaturerefluxed for 24 hours
  2. customMost of the ethanol was evaporated
  3. dissolutionThe residue was dissolved in water
  4. filtrationfiltered
  5. customto give an oily material which
  6. temperatureby cooling

Sources & evidence

ORD record
ord-a049529002dc4c8daf1d8684862da9f5
Source dataset
uspto-grants-2011_10
Patent number
US08034966B1

Reaction notes

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