Phenylacetyl chloride → Phenylacetic Acid

HRID 413521Notes

Reaction equation

HRID 413521 reaction equation
C(C(CCCC)C[OH:5])C.C(N(CC)CC)C.[C:17]1([CH2:23][C:24](Cl)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[C:17]1([CH2:23][C:24]([OH:25])=[O:5])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 77202-EthylhexanolHCID 8471Triethylamine

Product 1

HCID 999Phenylacetic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Mix 2-ethyl-1-hexanol (6.5 g, (5 mol), triethylamine (50.5 g, 0.5 mol) and methylene chloride (50 mL). Add, by dropwise addition, 2-phenylacetyl chloride (5 mol) and warm to 50° C. Stir a zoom temperature overnight, filter and wash the filtercake with methylene chloride (50 mL). Combine the organic phases and wash with it aqueous hydrochloric acid (50 mL) and water. Dry (MgSO4), evaporate the solvent in vacuo and purify by distillation to give 2-phenylacetic acid, 2-(2-ethylhexy)1 ester.

Workup

  1. filtrationfilter
  2. washwash the filtercake with methylene chloride (50 mL)
  3. washCombine the organic phases and wash with it aqueous hydrochloric acid (50 mL) and water
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. distillationpurify by distillation

Sources & evidence

ORD record
ord-ccd7bd242fa24d149be1a9e57fd9f654
Source dataset
uspto-grants-2003_05
Patent number
US06566526B2

Reaction notes

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