Acetic Acid → Phenoxyacetic Acid

HRID 1053527Notes

Reaction equation

HRID 1053527 reaction equation
[O:1]([CH2:8][C:9]([O:11]CC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(O)(=O)C>C1COCC1.O>[O:1]([CH2:8][C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 17365Acetic acid, 2-phenoxy-, ethyl ester

Product 1

HCID 19188Phenoxyacetic AcidYield 94.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 34 (2 g, 0.011 mol) was dissolved in 100 mL of THF, and 1 M NaOH (110 mL, 0.11 mol) was added. The reaction mixture was stirred at RT for 24 h. The solution was then acidified by the addition of 40 mL of acetic acid. The reaction mixture was diluted with 150 mL of H2O and the product was extracted with ethyl acetate. The organic extracts were dried over magnesium sulfate and concentrated. The crude product was washed several times with hexane:ethylacetate (9:1) to give a pale white solid (1.58 g, 94%). 1H NMR (300 MHz, CD2Cl2) δ 4.69 (s, 2H), 6.92 (d, J=8.2 Hz, 2H), 7.03 (t, J=7.0 Hz, 1H), 7.32 (t, J=7.6 Hz, 2H).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. dry with materialThe organic extracts were dried over magnesium sulfate
  3. concentrationconcentrated
  4. washThe crude product was washed several times with hexane:ethylacetate (9:1)

Sources & evidence

ORD record
ord-507887c3c4da4fc3b7daeb41f22b033c
Source dataset
uspto-grants-2016_07
Patent number
US09393306B2

Reaction notes

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