Acetic Acid → HCID 68154567, compound

HRID 1615733Notes

Reaction equation

HRID 1615733 reaction equation
CC(C)([O-])C.[Na+].[CH2:7]([O:9][C:10]([CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][C:18]([O:20]CC)=O)=[O:11])[CH3:8].C(O)(=O)C>C1COCC1>[O:20]=[C:18]1[CH2:17][O:16][CH2:15][CH2:14][O:13][CH:12]1[C:10]([O:9][CH2:7][CH3:8])=[O:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 13237171Diethyl 2,2'-[ethane-1,2-diylbis(oxy)]diacetateHCID 23676156Sodium t-butoxide

Product 1

HCID 68154567HCID 68154567, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The mixing was carried out under a protective nitrogen gas atmosphere. 7.93 g (80.0 mmol) sodium-tert-butoxide were placed in 150 ml THF and heated to boiling point. At this temperature 8.50 g (36.3 mmol) ethyl (2-ethoxycarbonylmethoxy-ethoxy)-acetate (prepared analogously to Canadian Journal of Chemistry; 74; 8; 1996; 1437-1446) in 100 ml THF were added dropwise within 3 h. After the addition had ended the mixture was refluxed for 1 h and then stirred overnight at RT. Then the reaction mixture was adjusted to pH 5 with glacial acetic acid and concentrated by rotary evaporation. The residue was mixed with water and extracted with ethyl acetate. The organic phases were combined, dried and the solvent was eliminated under reduced pressure and with gentle heating.

Workup

  1. temperatureheated
  2. additionAfter the addition
  3. temperaturewas refluxed for 1 h
  4. concentrationconcentrated by rotary evaporation
  5. additionThe residue was mixed with water
  6. extractionextracted with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-6942a0b85eb34e349f9724834d555e26
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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