Sulfuric Acid → HCID 15097814, compound

HRID 232210Notes

Reaction equation

HRID 232210 reaction equation
[O:1]=[C:2]1[O:6][CH:5]([C:7]([OH:9])=[O:8])[CH2:4][CH2:3]1.S(=O)(=O)(O)O.[CH2:15]=[C:16]([CH3:18])[CH3:17].C(=O)([O-])O.[Na+]>ClCCl>[O:1]=[C:2]1[O:6][CH:5]([C:7]([O:9][C:16]([CH3:18])([CH3:17])[CH3:15])=[O:8])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 2515245-Oxo-2-tetrahydrofurancarboxylic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 15097814HCID 15097814, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 100 ml of dichloromethane was dissolved 5.0 g of 5-oxo-2-tetrahydrofurancarboxylic acid. To the solution was added 0.3 ml of concentrated sulfuric acid at -60° C., to which was added an excess volume of isobutene (about 50 ml). The reaction mixture was allowed to stand at room temperature overnight in a sealed vessel, which was then poured into a cooled aqueous solution of sodium hydrogen carbonate. The dichloromethane layer was taken, washed with water and dried (Na2SO4), followed by concentration to give t-butyl 5-oxo-2-tetrahydrofurancarboxylate as colorless oil.

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-f8bd172bc32c400f9ea31a4e211db9b0
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Reaction notes

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