Water → HCID 20559492, compound

HRID 1659561Notes

Reaction equation

HRID 1659561 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]([OH:18])[CH3:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.Br[CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22].O>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]([O:18][CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH3:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79040Ethyl 2-bromopropionateHCID 20559498HCID 20559498, compound

Product 1

HCID 20559492HCID 20559492, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.7 g., 80% w/w suspension in mineral oil) was added gradually to a stirred solution of 1-[4-(4-chlorophenyl)phenyl]ethanol (4.7 g.) in dry dimethylformamide (20 ml.), keeping the temperature below 40° C. After 30 minutes stirring ethyl 2-bromopropionate (2.6 ml.) was then added, keeping the temperature below 30° C. After stirring for 16 hours at room temperature, the mixture was poured into water (150 ml.), and the subsequent mixture was extracted with ether. The combined extracts were washed with water, dried (MgSO4) and evaporated to give ethyl 2-{1-[4-(4-chlorophenyl)phenyl]ethoxy}propionate, as an oil (3.0 g.).

Workup

  1. customthe temperature below 40° C
  2. additionwas then added
  3. customthe temperature below 30° C
  4. extractionthe subsequent mixture was extracted with ether
  5. washThe combined extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-f01d3bee2dd14471a7512847d8ddfb47
Source dataset
uspto-grants-1981_12
Patent number
US04304788

Reaction notes

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