2-Butoxyethanol → 2-Butoxyethyl Levulinate

HRID 25892

Reaction equation

HRID 25892 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7]O)[CH2:2][CH2:3][CH3:4].[C:9]([OH:16])(=[O:15])[CH2:10][CH2:11][C:12]([CH3:14])=[O:13].CCCCCCCC(O[Sn](OC(CCCCCCC)=O)(CCCC)CCCC)=O>C1(C)C(C)=CC=CC=1>[C:9]([O:16][CH2:7][CH2:6][O:5][CH2:1][CH2:2][CH2:3][CH3:4])(=[O:15])[CH2:10][CH2:11][C:12]([CH3:14])=[O:13]

Participants

5

Reactant 3

HCID 81332-ButoxyethanolHCID 11579Levulinic AcidHCID 16683953Dibutyltin dioctanoate

Product 1

HCID 213256432-Butoxyethyl Levulinate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2 -Butoxyethanol (Butyl Cellosolve) 354g (3 mol), 232g (2 mol) levulinic acid and 1.5g dibutyl tin dioctoate were heated with a xylene azeotrope for 24 hours 151°-177° to AN 2.3 while collecting 42g water. Product was washed with sat. NaHCO3 and water, dried with anhy. MgSO4 and distilled. Ester product was collected in fr 2 and 3 120°-131° 1 mm. Yield was 349g, 81%, 96% ester product by gc.

Workup

  1. customwhile collecting 42g water
  2. washProduct was washed with sat. NaHCO3 and water
  3. customdried with anhy
  4. distillationMgSO4 and distilled
  5. customEster product was collected in fr 2 and 3 120°-131° 1 mm
  6. customYield

Sources & evidence

ORD record
ord-abc3c1bef80649e3acc4e6b3f41db6cd
Source dataset
uspto-grants-1979_04
Patent number
US04147686

Linked notes

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