Ethyl bromoacetate → HCID 10264196, compound

HRID 430028Notes

Reaction equation

HRID 430028 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C)C=O>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1)[CH3:21]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8434EthylparabenHCID 24758Sodium hydride

Product 1

HCID 10264196HCID 10264196, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2 g (12 mmole) of ethyl 4-hydroxybenzoate were added to a N,N-dimethylformamide (10 ml) suspension including 0.32 g of sodium hydride under ice cooling. Furthermore, a N,N-dimethylformamide (5 ml) solution including 2.2 g (13 mmole) of ethyl bromoacetate was added dropwise thereto, and reaction was then carried out for 15 hours. After the reaction mixture had been concentrated, partition was carried out between ethyl acetate and water. The organic layer was then treated in an ordinary manner to obtain 2.9 g (yield: 96%) of ethyl 4-(2-ethoxy-2-oxo-ethoxy)benzoate.

Workup

  1. additionwas added dropwise
  2. customreaction
  3. concentrationAfter the reaction mixture had been concentrated
  4. custompartition
  5. additionThe organic layer was then treated in an ordinary manner

Sources & evidence

ORD record
ord-fa588b51b3fc4d0fb61350eec20ad7d5
Source dataset
uspto-grants-2001_11
Patent number
US06320078B1

Reaction notes

Loading…