Benzyl Alcohol → (Benzyloxy)acetic acid

HRID 529280Notes

Reaction equation

HRID 529280 reaction equation
[OH-].[K+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH2:12][C:13]([OH:15])=[O:14].O>C1COCC1.CC(OC)(C)C>[CH2:3]([O:10][CH2:12][C:13]([OH:15])=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 300Chloroacetic AcidHCID 962WaterHCID 14797Potassium Hydroxide

Product 1

HCID 290301(Benzyloxy)acetic acidYield 70.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of KOH (17.84 g, 118 mmol) in THF (200 mL) was added benzyl alcohol (42 mL, 424 mmol). After 1.5 h the mixture was heated to 50° C. for 1.5 h and cooled to rt afterwards. Chloroacetic acid (10 g, 106 mmol) was added and the mixture was heated to 80° C. After 1.5 h the mixture was cooled to rt and water and MTBE was added. The layers were separated, the aqueous layer was extracted with MTBE, the pH of the aqueous layer was adjusted to pH=2 with 6N HCl and extracted with MTBE. The extracts of the acidic layer were dried and the solvent removed under reduced pressure to give 12.4 g of the crude product.

Workup

  1. temperaturecooled to rt afterwards
  2. temperaturethe mixture was heated to 80° C
  3. temperatureAfter 1.5 h the mixture was cooled to rt
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with MTBE
  6. extractionextracted with MTBE
  7. customThe extracts of the acidic layer were dried
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-a847121ec5ac4845985f1e19ce84b1b6
Source dataset
uspto-grants-2016_05
Patent number
US09346853B2

Reaction notes

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