Hydrochloric Acid → 5-(4-Chlorophenyl)-5-oxopentanoic acid

HRID 400237Notes

Reaction equation

HRID 400237 reaction equation
[Br-].[Al+3].[Br-].[Br-].[C:5]1(=[O:12])[O:11][C:9](=[O:10])[CH2:8][CH2:7][CH2:6]1.[ClH:13].CCO[C:17]([CH3:19])=O>ClC1C=CC=CC=1>[Cl:13][C:17]1[CH:19]=[CH:8][C:7]([C:9](=[O:10])[CH2:8][CH2:7][CH2:6][C:5]([OH:11])=[O:12])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7940Glutaric anhydrideHCID 8857Ethyl AcetateHCID 166749Bromhydrol

Product 1

HCID 27337165-(4-Chlorophenyl)-5-oxopentanoic acid

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

To a stirred solution of aluminium bromide (300 g, 1.12 mol) in dry chlorobenzene (700 ml) at 4° C. was added a solution of glutaric anhydride (60 g, 0.526 mol) in chlorobenzene (300 ml). The resulting orange/yellow suspension was allowed to warm to RT, stirred overnight, then carefully poured into an ice cold stirred solution of 10% HCl (aqueous 1400 ml). The resulting white suspension was poured into EtOAc (900 ml) and the layers separated. The aqueous layer was washed with EtOAc (2×250 ml). The combined organic layer was washed with brine (1×400 ml), dried (MgSO4) and the solvent removed in vacuo to give a yellow/white solid (115.74 g). Recrystallization from toluene/hexane (2:1, 750 ml) gave the title compound (95.14 g) as off white crystals.

Workup

  1. customthe layers separated
  2. washThe aqueous layer was washed with EtOAc (2×250 ml)
  3. washThe combined organic layer was washed with brine (1×400 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-279f2eab3df44322813bd4c349d78125
Source dataset
uspto-grants-1998_10
Patent number
US05827890

Reaction notes

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