Hydrochloric Acid → 2-Butoxyethoxy Levulinate

HRID 25891

Reaction equation

HRID 25891 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][OH:8])[CH2:2][CH2:3][CH3:4].[CH2:9](O)[C:10]1[O:14]C=[CH:12][CH:11]=1.Cl.[C:17]([O-:20])(O)=[O:18].[Na+]>>[C:17]([O:20][O:8][CH2:7][CH2:6][O:5][CH2:1][CH2:2][CH2:3][CH3:4])(=[O:18])[CH2:12][CH2:11][C:10]([CH3:9])=[O:14]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7361Furfuryl AlcoholHCID 81332-Butoxyethanol2×HCID 516892Sodium Bicarbonate

Product 1

HCID 213256412-Butoxyethoxy Levulinate

Procedure

2-Butoxyethanol (Butyl Cellosolve) 47.2g (0.4 mol) and 157g (1.6 mol) furfuryl alcohol were added to 422g (3.9 mol) 2-butoxyethanol and 7.2g conc. HCl over 11/2 hours at 109°-114° and held at 108° for an additional 11/2 hours. Reaction product was neutralized with sat. NaHCO3, washed with water, dried with anhy. MgSO4 and distilled. 2-Butoxyethyl levulinate was collected in fr 2 95°-106° 1 mm, 95% ester by gc.

Workup

  1. customheld at 108° for an additional 11
  2. custom2 hours
  3. customReaction product
  4. washwashed with water
  5. customdried with anhy
  6. distillationMgSO4 and distilled
  7. custom2-Butoxyethyl levulinate was collected in fr 2 95°-106° 1 mm, 95% ester by gc

Sources & evidence

ORD record
ord-857833e427d4400aa00faeb8842693d5
Source dataset
uspto-grants-1979_04
Patent number
US04147686

Linked notes

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