Potassium Carbonate → HCID 17817500, compound

HRID 1356442Notes

Reaction equation

HRID 1356442 reaction equation
C([CH:3]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[C:4]([OH:6])=[O:5])C.C(=O)([O-])[O-].[K+].[K+].[C:20]1([C:26]2[CH:33]=[CH:32][C:29]([CH2:30]Cl)=[CH:28][CH:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C.C(OCC)(=O)C>[C:26]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:27]=[CH:28][C:29]([CH2:30][O:13][C:10]2[CH:9]=[CH:8][C:7]([CH2:3][C:4]([OH:6])=[O:5])=[CH:12][CH:11]=2)=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 154634-Phenylbenzyl chlorideHCID 346562-(4-Hydroxyphenyl)butanoic acid

Product 1

HCID 17817500HCID 17817500, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 4-hydroxyphenylacetic acid (3.6 g) in DMF (50 ml) were added potassium carbonate (2.5 g) and 4-phenylbenzyl chloride (4 g) sequentially. After stirring at 60° C. for 6 hr, the reaction mixture was poured onto water and the resulting crystals were suspended in ethyl acetate. The suspension was washed with water and concentrated. The resulting crude crystals were dissolved in THF (100 ml)/ethanol (50 ml) and 2 N sodium hydroxide (20 ml) was added to the solution. The reaction mixture was heated under stirring at 60° C. for 18 hr and concentrated. The residue was acidified with 2 N hydrochloric acid and the resulting crystals were collected by filtration and washed with ethyl ether to obtain the titled compound (5.3 g).

Workup

  1. additionthe reaction mixture was poured onto water
  2. washThe suspension was washed with water
  3. concentrationconcentrated
  4. dissolutionThe resulting crude crystals were dissolved in THF (100 ml)/ethanol (50 ml) and 2 N sodium hydroxide (20 ml)
  5. additionwas added to the solution
  6. temperatureThe reaction mixture was heated
  7. stirringunder stirring at 60° C. for 18 hr
  8. concentrationconcentrated
  9. filtrationthe resulting crystals were collected by filtration
  10. washwashed with ethyl ether

Sources & evidence

ORD record
ord-3463aa3e011240a0ae764ab68a912486
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

Loading…