Sodium Acetate → 2-[(Acetyloxy)methyl]4-(2-chloroethoxy)-5-methoxybenzyl acetate

HRID 989350Notes

Reaction equation

HRID 989350 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([CH2:11]Cl)[C:8]([CH2:13]Cl)=[CH:7][C:6]=1[O:15][CH3:16].[C:17]([O-:20])(=[O:19])[CH3:18].[Na+]>C(O)(=O)C>[C:17]([O:20][CH2:13][C:8]1[CH:7]=[C:6]([O:15][CH3:16])[C:5]([O:4][CH2:3][CH2:2][Cl:1])=[CH:10][C:9]=1[CH2:11][O:20][C:17](=[O:19])[CH3:18])(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 117161401-(2-Chloroethoxy)-4,5-bis(chloromethyl)-2-methoxybenzene

Product 1

HCID 115879752-[(Acetyloxy)methyl]4-(2-chloroethoxy)-5-methoxybenzyl acetateYield 86%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 5.67 g (0.020 mole) of 1-(2-chloroethoxy)-4,5-bis(chloromethyl)-2-methoxybenzene in 75 ml acetic acid is added a solution of 3.5 g of anhydrous sodium acetate in 100 ml acetic acid. This mixture is refluxed with stirring for 2 hours. Solids are removed by filtration and washed with acetic acid. The filtrate is evaporated to approximately 30 ml, then poured into water and extracted with ether. The organic phase is washed with aqueous sodium carbonate, water and brine. After drying over sodium sulfate, the solution is filtered and evaporated to give 5.69 g (86%) of 2-[(acetyloxy)methyl]-4-(2-chloroethoxy)-5-methoxybenzyl acetate as a white solid, m.p. 79-80° C.

Workup

  1. temperatureThis mixture is refluxed
  2. customSolids are removed by filtration
  3. washwashed with acetic acid
  4. customThe filtrate is evaporated to approximately 30 ml
  5. additionpoured into water
  6. extractionextracted with ether
  7. washThe organic phase is washed with aqueous sodium carbonate, water and brine
  8. dry with materialAfter drying over sodium sulfate
  9. filtrationthe solution is filtered
  10. customevaporated

Sources & evidence

ORD record
ord-758176609f1f49e9bb31f95513ede4a2
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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