Hydrochloric Acid → 2-(4-Isobutyrylphenyl)ethyl acetate

HRID 384587Notes

Reaction equation

HRID 384587 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[Cl-].[Al+3].[Cl-].[Cl-].[C:11]([O:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:13])[CH3:12].Cl>C(Cl)Cl>[C:11]([O:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])=[CH:19][CH:18]=1)(=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76542-Phenylethyl AcetateHCID 62325Isobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 688611852-(4-Isobutyrylphenyl)ethyl acetateYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isobutyryl chloride (114 g, 1.07 mol) is added drop wise at −5 to 0° C. over 40 minutes to 295 g (2.21 mol) of anhydrous aluminum chloride in 160 ml of methylene chloride. Stirring is continued for 30 min, and 2-phenylethyl acetate (164.2 g, 1.00 mol) is then added drop wise at −5 to 0° C. over 2 hours. The mixture is stirred an additional 4 hours at −5 to 0° C., and then poured into a mixture of concentrated hydrochloric acid and ice. The organic layer is washed with water, dried and concentrated to give 190.5 g of crude 2-(4-isobutyrylphenyl)ethyl acetate, a colorless liquid.

Workup

  1. stirringThe mixture is stirred an additional 4 hours at −5 to 0° C.
  2. washThe organic layer is washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cd030ecfde6e43b3854960ce82c721d0
Source dataset
uspto-grants-2013_02
Patent number
US08367743B2

Reaction notes

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