2-Butoxyethanol → 2-Butoxyethyl Levulinate

HRID 2083182Notes

Reaction equation

HRID 2083182 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 (2mol) 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-427e9db14921449a8f9e69504bb06cab
Source dataset
uspto-grants-1978_04
Patent number
US04085081

Reaction notes

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