Water → 4-(4-Fluorobenzoyl)butyric Acid

HRID 395586Notes

Reaction equation

HRID 395586 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1(=[O:12])[O:11][C:9](=[O:10])[CH2:8][CH2:7][CH2:6]1.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>ClCCl>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:9](=[O:10])[CH2:8][CH2:7][CH2:6][C:5]([OH:11])=[O:12])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7940Glutaric anhydrideHCID 10008FluorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 6890964-(4-Fluorobenzoyl)butyric AcidYield 57.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 22.32 g (0.167 mol) of aluminum chloride in 35 ml of dichloromethane is prepared. It is cooled to 0° C. and a mixture of 8.3 g (0.0728 mol) of glutaric anhydride (dihydro-2H-pyran-2,6(3H)-dione) and 8.4 ml (0.0895 mol) of fluorobenzene in 20 ml of dichloromethane is added slowly. The mixture is stirred for 15 hours at room temperature and then hydrolyzed in acidified iced water. The precipitated product is filtered off, washed with water and then dried under reduced pressure. The crude product is then recrystallized from 90 ml of ethyl acetate to give 8.8 g of the expected product in the form of beige crystals (yield=57.5%).

Workup

  1. customis prepared
  2. additionis added slowly
  3. filtrationThe precipitated product is filtered off
  4. washwashed with water
  5. customdried under reduced pressure
  6. customThe crude product is then recrystallized from 90 ml of ethyl acetate

Sources & evidence

ORD record
ord-ed8d4152b8134b02b92b6a3a4397c163
Source dataset
uspto-grants-2003_08
Patent number
US06605633B1

Reaction notes

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