Methanol → HCID 19764144, compound

HRID 2371658Notes

Reaction equation

HRID 2371658 reaction equation
[C:1]([O:4][CH2:5]C)(=[O:3])[CH3:2].[CH3:7][O-:8].[Na+].[Br:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14]Br.[CH3:19]O>>[Br:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][CH:2]([C:7]([CH3:19])=[O:8])[C:1]([O:4][CH3:5])=[O:3]

Participants

5

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 699793-Bromobenzyl bromideHCID 10942334Sodium Methoxide

Product 1

HCID 19764144HCID 19764144, compoundYield 80%

Procedure

58 g (0.5 mol) of ethyl acetate are rapidly added dropwise to a solution of 13.5 g (0.25 mol) of sodium methylate in 100 ml of methanol, at 30°-35° C. After the mixture is stirred for a short while (20 minutes), 50 g (0.25 mol) of 3-bromobenzyl bromide are added dropwise at 30° C. After the exothermic reaction has ceased, the mixture is heated at the boil for another 4 hours, and the solvent is subsequently distilled off. The residue is treated with 200 ml of water, and the mixture is extracted 3 times with 75 ml of ether. The combined organic phases are dried over sodium sulphate and freed from the solvent. Fractionation of the residue gives 56.0 g (0.20 mol, 80% of theory) of methyl 2-(3-bromobenzyl)acetoacetate of boiling point 105° C./0.1 torr).

Workup

  1. additionare added dropwise at 30° C
  2. customAfter the exothermic reaction
  3. temperaturethe mixture is heated at the boil for another 4 hours
  4. distillationthe solvent is subsequently distilled off
  5. additionThe residue is treated with 200 ml of water
  6. extractionthe mixture is extracted 3 times with 75 ml of ether
  7. dry with materialThe combined organic phases are dried over sodium sulphate

Sources & evidence

ORD record
ord-2ccbec8351ba492bb2b387af2995630a
Source dataset
uspto-grants-1992_03
Patent number
US05094681

Reaction notes

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