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

HRID 408448Notes

Reaction equation

HRID 408448 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 (20 mmol) of 36 in 75 mL of acetic acid was added a solution of 3.5 g of anhydrous sodium acetate (42.7 mmol) in 100 mL of acetic acid. This mixture was refluxed with stirring for 2 h. Solids were removed by filtration and washed with acetic acid. The filtrate was evaporated to approximately 30 mL, then poured into water and extracted with ether. The organic phase was washed with aqueous sodium carbonate, water, and brine. After drying over sodium sulfate, the solution was filtered and evaporated to give 5.69 g (86%) of 2-[(acetyloxy)methyl]-4-(2-chloroethoxy)-5-methoxybenzyl acetate (37) as a white solid, mp 79-80° C.

Workup

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

Sources & evidence

ORD record
ord-d8574a2add784f29906a8129f6c6f30e
Source dataset
uspto-grants-2014_06
Patent number
US08759339B2

Reaction notes

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