Sodium Hydroxide → Diethyl 2-(3-butenyloxy)terephthalate

HRID 260416Notes

Reaction equation

HRID 260416 reaction equation
[OH:1][C:2]1[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[OH-].[Na+].Br[CH2:21][CH2:22][CH:23]=[CH2:24]>CN(C)C=O>[CH2:24]([O:1][C:2]1[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:23][CH:22]=[CH2:21]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21241Homoallyl bromideHCID 22401614Diethyl 2-hydroxybenzene-1,4-dicarboxylate

Product 1

HCID 22401611Diethyl 2-(3-butenyloxy)terephthalateYield 39.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3.55 g of this diethyl hydroxyterephthalate was dissolved in 100 mL dimethylformamide and combined with 640 mg of crushed sodium hydroxide. 4.03 g of 4-bromo-1-butene dissolved in 20 mL of dimethylformamide was added dropwise in while cooling on an ice bath. After stirring the reaction for 16 hours, purification by the usual methods gave 1.74 g of diethyl 2-(3-butenyloxy)terephthalate.

Workup

  1. additionwas added dropwise in
  2. temperaturewhile cooling on an ice bath
  3. customthe reaction for 16 hours
  4. custompurification by the usual methods

Sources & evidence

ORD record
ord-c7bd1eecbcbf48718644374b9d43c475
Source dataset
uspto-grants-1996_06
Patent number
US05527862

Reaction notes

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