Sulfuric Acid → HCID 54720230, compound

HRID 985429Notes

Reaction equation

HRID 985429 reaction equation
[OH:1][C:2]1[CH:6]([CH3:7])[O:5][C:4](=[O:8])[CH:3]=1.[C:9](O)([CH3:12])([CH3:11])[CH3:10].S(=O)(=O)(O)O>>[C:9]([C:3]1[C:4](=[O:8])[O:5][CH:6]([CH3:7])[C:2]=1[OH:1])([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 5469215222885-98-9

Product 1

HCID 54720230HCID 54720230, compoundYield 13%

Conditions

Temperature
40 °C

Procedure

4-Hydroxy-5-methyl-5H-furan-2-one (15.9 g, 0.14 mol) was dissolved in tert-butanol (13.9 ml, 0.147 mol) with concentrated sulfuric acid (7.8 ml, 0.147 mol) and heated at 40° C. for 4 days. The reaction mixture was allowed to cool and was partitioned between water (75 ml) and diethyl ether (75 ml). The organic layer was separated and dried (Na2SO4), filtered and concentrated under vacuum. Chromatography on silica gel with diethyl ether as eluent gave a crude product which was further purified by chromatography on silica gel with dichloromethane as eluent then triturated with diethyl ether to give 3-tert-butyl-4-hydroxy-5-methyl-5H-furan-2-one (3.1 g) as a white solid. 1H NMR (360 MHz, CDCl3) δ 1.34 (9H, s), 1.46 (3H, d, J=6.7 Hz), 4.69 (1H, q, J=6.7 Hz).

Workup

  1. temperatureto cool
  2. customwas partitioned between water (75 ml) and diethyl ether (75 ml)
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customChromatography on silica gel with diethyl ether as eluent gave a crude product which
  8. customwas further purified by chromatography on silica gel with dichloromethane as eluent
  9. customthen triturated with diethyl ether

Sources & evidence

ORD record
ord-f9f54c0bd3e94126a169a4d41cb4db97
Source dataset
uspto-grants-2005_03
Patent number
US06872720B2

Reaction notes

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