4-Hydroxybenzophenone → HCID 14010386, compound

HRID 2292191Notes

Reaction equation

HRID 2292191 reaction equation
[CH3:1][C:2]([CH3:9])([C:6](Cl)=[O:7])[C:3](Cl)=[O:4].[OH:10][C:11]1[CH:24]=[CH:23][C:14]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])=[CH:13][CH:12]=1.C(OCC)(=[O:27])C.O>C(Cl)Cl.N1C=CC=CC=1>[CH3:1][C:2]([C:6]([OH:27])=[O:7])([CH3:9])[C:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])=[CH:23][CH:24]=1)=[O:4]

Participants

6

Reactant 3

HCID 143474-HydroxybenzophenoneHCID 4523180Dimethylmalonyl DichlorideHCID 22728543Water ethylacetate

Product 1

HCID 14010386HCID 14010386, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2 g (12 mmol) of dimethylmalonyl chloride in 19 ml of methylene chloride, a solution of 2 g (10 mmol) of 4-hydroxybenzophenone in 10 ml of pyridine was added over 15 min at -5° C. The mixture was stirred at 0° C. for 0.5 h, allowed to warm to 25° C. over 1 h, then stripped of the solvent, and finally stirred with 1:1 ethyl acetate-water for 1.5 h at 25° C. The organic phase was washed with cold 2% hydrochloric acid, then with water, and finally extracted with 5% sodium bicarbonate solution. The aqueous extract was acidified to pH 3 and filtered to collect crude product, which was purified by recrystallization from EtOH-water to yield the title compound. 0.325 g (10%); M.P.~147°-150° C.

Workup

  1. temperatureto warm to 25° C. over 1 h
  2. washThe organic phase was washed with cold 2% hydrochloric acid
  3. extractionwith water, and finally extracted with 5% sodium bicarbonate solution
  4. extractionThe aqueous extract
  5. filtrationfiltered
  6. customto collect crude product, which
  7. customwas purified by recrystallization from EtOH-water

Sources & evidence

ORD record
ord-98e56ae51a7841beb2dfa97a59aa88e6
Source dataset
uspto-grants-1989_01
Patent number
US04801610

Reaction notes

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