Sodium Hydroxide → DL-2-Phenoxypropionic acid

HRID 1429439Notes

Reaction equation

HRID 1429439 reaction equation
[O:1]([CH:8]([CH3:14])[C:9]([O:11]CC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CCO.O>[O:1]([CH:8]([CH3:14])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 4496358HCID 4496358, compound

Product 1

HCID 13658DL-2-Phenoxypropionic acidYield 735.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 2-phenoxypropanoate (1.8 g, 0.9 mmol) in EtOH (16 ml) was added a solution of NaOH (0.44 g, 1.1 mmol) in H2O (4 ml) at 25° C. The mixture was stirred for 30 min before being concentrated. The residue had water (20 mL) added and washed with ethyl acetate (2×20 mL). The aqueous layer was acidified with 2N HCL until pH 3 and extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to give the title compound (1.1 g, 73.3%) as a white solid which was used in next step without further purification.

Workup

  1. concentrationbefore being concentrated
  2. additionadded
  3. washwashed with ethyl acetate (2×20 mL)
  4. extractionextracted with ethyl acetate (2×20 mL)
  5. washThe combined organic layers were washed with brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-495a3aa11947454c9462203c5dd64c68
Source dataset
uspto-grants-2015_01
Patent number
US08940726B2

Reaction notes

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