Sulfuric Acid → HCID 86758304, compound

HRID 2227496Notes

Reaction equation

HRID 2227496 reaction equation
[CH:1]([C:3]1[CH:22]=[CH:21][C:6]([CH:7]=[CH:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[O:10])=[CH:5][CH:4]=1)=[O:2].Br[CH2:24][C:25]([O:27][CH3:28])=[O:26].S(=O)(=O)(O)O>C1C=CC=CC=1.[Zn]>[OH:2][CH:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:7]=[CH:8][C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[O:10])=[CH:21][CH:22]=1)[CH2:24][C:25]([O:27][CH3:28])=[O:26]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 60984Methyl bromoacetateHCID 86758303p-Anisyl 4-formylcinnamate

Product 1

HCID 86758304HCID 86758304, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 241BenzeneSolvent

Procedure

Next, 296 mg of p-anisyl 4-formylcinnamate and 0.14 ml of methyl bromoacetate were dissolved in 4 ml benzene, and mixed with 95 mg of zinc powder to form a suspension, followed by heating under a stream of argon for 5 hours. The reaction mixture was allowed to cool, mixed with 10% sulfuric acid, extracted with ether and then washed with 5% sulfuric acid. The organic layer was washed with 10% aqueous sodium carbonate, and dried over magnesium sulfate. The drying agent was filtered off and the filtrate was evaporated under reduced pressure and dried to give p-anisyl 4-[1-hydroxy-2-(methoxycarbonyl)ethyl]-cinnamate of interest (51 mg, 14%) as a pale yellow liquid.

Workup

  1. customto form a suspension
  2. temperatureby heating under a stream of argon for 5 hours
  3. temperatureto cool
  4. extractionextracted with ether
  5. washwashed with 5% sulfuric acid
  6. washThe organic layer was washed with 10% aqueous sodium carbonate
  7. dry with materialdried over magnesium sulfate
  8. filtrationThe drying agent was filtered off
  9. customthe filtrate was evaporated under reduced pressure
  10. customdried

Sources & evidence

ORD record
ord-2e24cd3fb0d343e3835adfc351055ebb
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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