Benzene → HCID 18473835, compound

HRID 2227507Notes

Reaction equation

HRID 2227507 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:18]=[CH:17][C:8]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1.C1C=CC=CC=1.II.S(=O)(=O)(O)O.Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>[Zn].O.C1(C)C=CC=CC=1>[OH:10][C:9]([C:8]1[CH:17]=[CH:18][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:6][CH:7]=1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]

Participants

9

Reactant 5

HCID 241BenzeneHCID 807IodineHCID 1118Sulfuric AcidHCID 7748Ethyl bromoacetateHCID 18473836HCID 18473836, compound

Product 1

HCID 18473835HCID 18473835, compoundYield 39.9%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

0.485 g of 4-(methoxymethoxy)benzophenone was dissolved in 0.45 ml ethyl bromoacetate, 1.5 ml benzene and 1.5 ml toluene, mixed with 3.27 g of zinc and 50 mg of iodine, and then refluxed for 2 hours under a stream of argon. The reaction mixture was mixed with water, adjusted to pH 1 with concentrated sulfuric acid, and then extracted with benzene three times. The extract was filtrated to remove insoluble components, washed twice with water and once with brine, followed by drying over anhydrous magnesium sulfate. The drying agent was filtered off and the filtrate was evaporated and purified via column chromatography on silica gel (ethyl acetate:hexane=1:5) to give ethyl 3-hydroxy-3-[4-(methoxymethoxy)phenyl]-3-phenylpropionate (263 mg, yield: 39.9%) as an oil.

Workup

  1. temperaturerefluxed for 2 hours under a stream of argon
  2. extractionextracted with benzene three times
  3. filtrationThe extract was filtrated
  4. customto remove insoluble components
  5. washwashed twice with water and once with brine
  6. dry with materialby drying over anhydrous magnesium sulfate
  7. filtrationThe drying agent was filtered off
  8. customthe filtrate was evaporated
  9. custompurified via column chromatography on silica gel (ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-9e128ec3a1bc40ad9ddb3e02d70ca589
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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