Sodium Hydroxide → 3-(2,6-Dimethylbenzyloxy)phenylpropionic acid

HRID 2079926Notes

Reaction equation

HRID 2079926 reaction equation
[CH2:1]([C:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:23])[CH:9]=1)(C)[C:4]([O-:6])=[O:5])C.[OH-].[Na+]>C(O)C>[CH3:22][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:23])[C:16]=1[CH2:15][O:14][C:10]1[CH:9]=[C:8]([CH:3]([CH3:1])[C:4]([OH:6])=[O:5])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86608896Ethyl-3-(2,6-dimethylbenzyloxy)phenylpropionate

Product 1

HCID 578227133-(2,6-Dimethylbenzyloxy)phenylpropionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

9.3 g of an oil containing ˜60% ethyl-3-(2,6-dimethylbenzyloxy)phenylpropionate was dissolved in 75 ml of absolute ethanol in a single necked, 250 ml round bottom flask equipped with a stir bar and reflux condenser. 4.0 ml of 7.5N sodium hydroxide was added to the solution. The light yellow solution was heated to reflux (80° C.) and stirred for 1 hr. The reaction was analyzed and LC-MS showed the desired product and no starting ester. The reaction was cooled to room temperature and concentrated in vacuo to afford a yellow oil. The oil was dissolved in 25 ml of water and extracted 3× with 25 ml of ether. The aqueous layer was cooled to <5° C. in an ice bath and acidified to a pH=1 by slowly adding 15 ml of 6N aqueous HCl solution. The precipitated solid were collected by filtration, washed 3× with 25 ml of water and air-dried. The solids were slurried in 100 ml of hexanes and collect by filtration, washed 3× with 25 ml of hexanes and air-dried. LC-MS showed the solids to be ˜80% desired product. The solids were heated to 70° C. in 44 ml of 3:1, absolute ethanol:water mixture. The solution was stirred and allowed to cool to room temperature in a tap water bath. The solids were collected by filtration, washed with 20 ml of 3:1, absolute ethanol: water mixture and air-dried. LC-MS showed the solid to be ˜98.5% desired product. The solids were heated to 70° C. in 36 ml of 3:1, absolute ethanol: water mixture. The solution was stirred and allowed to cool to room temperature in a tap water bath. The solids were collected by filtration, washed with 20 ml of a 3:1, absolute ethanol: water mixture and air-dried. LC-MS and NMR showed the solids to be >99.5% desired product. The white solid was dried in a vacuum oven at 40° C. for 2 hrs. to afford 3.91 g (52.9%).

Workup

  1. customequipped with a stir bar
  2. temperaturereflux condenser
  3. temperatureThe light yellow solution was heated

Sources & evidence

ORD record
ord-a69678fa475b4e5296f405beeb1148a7
Source dataset
uspto-grants-2011_04
Patent number
US07932290B2

Reaction notes

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