Benzoic Acid → HCID 54023278, compound

HRID 1710220Notes

Reaction equation

HRID 1710220 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=[CH:25][O:26][CH3:27])[C:21]([O:23][CH3:24])=[O:22]>C(O)C>[C:1]([O:9][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=[CH:25][O:26][CH3:27])[C:21]([O:23][CH3:24])=[O:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 14797Potassium HydroxideHCID 53395349Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoate

Product 1

HCID 54023278HCID 54023278, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

12.2 g (0.1 mole) of benzoic acid and 5.6 g (0.1 mole) of potassium hydroxide are dissolved in 150 ml of ethanol and the solution is stirred for 2 hours at room temperature (20° C.). The white precipitate which separates out is filtered off under suction, washed with diethyl ether and suspended in 300 ml of dimethylformamide. Thereafter, 28.5 g (0.1 mole) of methyl alpha-(2-bromomethylphenyl)-β-methoxyacrylate are added. The reaction mixture is then stirred for 24 hours at room temperature, after which it is evaporated down and the residue is taken up in methylene chloride. The organic phase is washed with water, dried over MgSO4 and evaporated down. The oil obtained is chromatographed over silica gel using 10:1 cyclohexane/ethyl acetate. 25.4 g (78%) of the title compound are obtained as a colorless, viscous oil (compound No. 83).

Workup

  1. filtrationThe white precipitate which separates out is filtered off under suction
  2. washwashed with diethyl ether
  3. stirringThe reaction mixture is then stirred for 24 hours at room temperature
  4. customafter which it is evaporated down
  5. washThe organic phase is washed with water
  6. dry with materialdried over MgSO4
  7. customevaporated down
  8. customThe oil obtained
  9. customis chromatographed over silica gel using 10:1 cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-6313178fef3247e08697b85b127722cd
Source dataset
uspto-grants-1990_08
Patent number
US04952720

Reaction notes

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