Sodium Hydroxide → HCID 18548193, compound

HRID 1265994Notes

Reaction equation

HRID 1265994 reaction equation
C([O:3][C:4](=[O:15])[CH:5]([CH2:11][C:12]([Br:14])=[CH2:13])[C:6]([O:8]CC)=[O:7])C.[OH-].[Na+]>>[Br:14][C:12](=[CH2:13])[CH2:11][CH:5]([C:6]([OH:8])=[O:7])[C:4]([OH:15])=[O:3]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 13113430HCID 13113430, compound

Product 1

HCID 18548193HCID 18548193, compoundYield 63.2%

Procedure

A mixture of 10.5 g (0.0376 mol) of 2-(2-bromo-allyl)-malonic acid diethyl ester and 37.6 ml (0.470 mol) of 50% aqueous sodium hydroxide was stirred at room temperature for 4 days. The reaction mixture was extracted with diethyl ether. The isolated aqueous layer was acidified by the addition of concentrated hydrochloric acid and diethyl ether was added. The resulting mixture was transferred to a separatory funnel where the phases were separated. The isolated organic layer dried over magnesium sulfate and filtered. The solvent was removed from the filtrate in vacuo to yield 5.3 g of 2-(2-bromo-allyl)-malonic acid as a solid which was carried on without purification.

Workup

  1. extractionThe reaction mixture was extracted with diethyl ether
  2. additionThe isolated aqueous layer was acidified by the addition of concentrated hydrochloric acid and diethyl ether
  3. additionwas added
  4. customThe resulting mixture was transferred to a separatory funnel
  5. customwhere the phases were separated
  6. dry with materialThe isolated organic layer dried over magnesium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed from the filtrate in vacuo

Sources & evidence

ORD record
ord-2f4799e63e704fa1a4ba354990bd3728
Source dataset
uspto-grants-2003_04
Patent number
US06548448B2

Reaction notes

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