Potassium Carbonate → 1-{5'-[3,4-Bis(benzoyloxymethyl)benzyloxy]-2'methyl-2-propylbiphenyl-4-yl}-1-propanone

HRID 584292Notes

Reaction equation

HRID 584292 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:17])[CH2:15][CH3:16])=[CH:10][C:9]=2[CH2:18][CH2:19][CH3:20])[CH:7]=1.[C:22]([O:30][CH2:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[CH2:40][O:41][C:42](=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:35]Br)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[C:22]([O:30][CH2:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[CH2:40][O:41][C:42](=[O:49])[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[CH2:35][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:17])[CH2:15][CH3:16])=[CH:10][C:9]=2[CH2:18][CH2:19][CH3:20])[CH:7]=1)(=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 223455921-(5'-Hydroxy-2'-methyl-2-propylbiphenyl-4-yl)-1-propanoneHCID 223456183,4-Bis(benzoyloxymethyl)benzyl bromide

Product 1

HCID 223456301-{5'-[3,4-Bis(benzoyloxymethyl)benzyloxy]-2'methyl-2-propylbiphenyl-4-yl}-1-propanoneYield 56%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

1.5 g (5.4 mmol) of 1-(5′-hydroxy-2′-methyl-2-propylbiphenyl-4-yl)-1-propanone, 2.5 g (5.7 mmol) of (3,4-bis(benzoyloxymethyl)benzyl bromide and 750 mg (5.4 mmol) of potassium carbonate are placed in 50 ml of methyl ethyl ketone in a round-bottomed flask and under a stream of nitrogen. The mixture is refluxed overnight and, after cooling, it is filtered through Celite. The filtrate is extracted with water and ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and then evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (85/15) to give 1.93 g (56%) of the expected product in the form of a dark yellow oil.

Workup

  1. temperatureThe mixture is refluxed overnight
  2. temperatureafter cooling
  3. filtrationit is filtered through Celite
  4. extractionThe filtrate is extracted with water and ethyl acetate
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue obtained
  9. customis purified by chromatography on a column of silica
  10. washeluted with a mixture of heptane and ethyl acetate (85/15)

Sources & evidence

ORD record
ord-9a10ba9d8ca14987ade8df95d7112f3f
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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