Phenylacetyl chloride → Phenylacetic Acid

HRID 2306041Notes

Reaction equation

HRID 2306041 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 at room temperature overnight, filter and wash the filtercake with methylene chloride (50 mL). Combine the organic phases and wash with 5% 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 5% 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-6da0f2c8b360469995a715ee8d151b0e
Source dataset
uspto-grants-2002_08
Patent number
US06441179B1

Reaction notes

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