Acetate → Phenoxyacetic Acid

HRID 526663Notes

Reaction equation

HRID 526663 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[OH-:5].[K+].[CH3:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Cl>CO.C(OCC)(=O)C>[O:5]([CH2:2][C:1]([OH:4])=[O:3])[C:9]1[CH:8]=[CH:7][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 175AcetateHCID 313Hydrochloric AcidHCID 8058HexaneHCID 14797Potassium Hydroxide

Product 1

HCID 19188Phenoxyacetic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent3×

Procedure

A portion of 16a (15.8 g; 29.9 mmol) was dissolved in 748 mL of MeOH. 35% aq. KOH (262 mL) was added in portions over 5 min. The reaction was heated to reflux. After 1 h TLC (30% ethyl acetate:hexane) indicated no starting material remained. After 4 h, TLC (100% ethyl acetate) indicated a heavy UV active spot above the origin. The reaction mixture was cooled to RT, then placed in an ice bath. 2M HCl (600 mL) was added to acidify the reaction to pH 5. The reaction mixture was diluted with 1.6 L of ethyl acetate and washed with sat. NaCl (1.6 L). The organic layer was dried over anhydrous sodium sulfate. The solvent was filtered through a sintered glass funnel. The filtrate was concentrated in vacua to recover 15.1 g of 17 as viscous oil which was taken onto the next step.

Workup

  1. temperatureThe reaction was heated to reflux
  2. customplaced in an ice bath
  3. customthe reaction to pH 5
  4. washwashed with sat. NaCl (1.6 L)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationThe solvent was filtered through a sintered glass funnel
  7. concentrationThe filtrate was concentrated in vacua
  8. customto recover 15.1 g of 17 as viscous oil which

Sources & evidence

ORD record
ord-d9da9e4d95a247738730063744c3531d
Source dataset
uspto-grants-2016_05
Patent number
US09346738B2

Reaction notes

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