Sulfuric Acid → HCID 18406868, compound

HRID 1016401Notes

Reaction equation

HRID 1016401 reaction equation
[OH:1][C:2]1[CH2:3][C:4](=[O:7])[O:5][CH:6]=1.[C:8](O)([CH3:11])([CH3:10])[CH3:9].S(=O)(=O)(O)O>O>[C:8]([CH:3]1[C:2]([OH:1])=[CH:6][O:5][C:4]1=[O:7])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 221728094-Hydroxyfuran-2(3H)-one

Product 1

HCID 18406868HCID 18406868, compoundYield 7.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To 4-hydroxy-2-furanone (50 g, 0.5 mol) in tert-butanol (50 ml, 0.53 mol) was added concentrated sulfuric acid (25 ml). The mixture was heated at 40° C. for 20 h then allowed to cool. Water (250 ml) was added and the mixture was extracted with diethyl ether (3×250 ml), the diethyl ether layers were combined, washed with brine (250 ml), dried (Na2SO4), filtered and concentrated in vacuo to give a brown solid. The solid was purified by silica gel chromatography with 0%→100% ethyl acetate/isohexane as eluent followed by two recrystallisations from ethyl acetate/isohexane (1:1) to afford the required product (5.75 g). Data for the title compound: 1H NMR (400 MHz, DMSO) δ 1.21 (9H, s), 4.48 (2H, s), 11.40 (1H, s); MS (ES+) m/e 156 [MH]+.

Workup

  1. temperatureto cool
  2. extractionthe mixture was extracted with diethyl ether (3×250 ml)
  3. washwashed with brine (250 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a brown solid
  8. customThe solid was purified by silica gel chromatography with 0%→100% ethyl acetate/isohexane as eluent
  9. customfollowed by two recrystallisations from ethyl acetate/isohexane (1:1)

Sources & evidence

ORD record
ord-d8fc069aa3d845b5aa2229d29154ee54
Source dataset
uspto-grants-2002_11
Patent number
US06476030B1

Reaction notes

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