Reaction #2186167

ord-57713df33581498f99fa8fadf49d8c48

Reaction equation

CC(C)=O
acetone
O=S(=O)(O)O
sulfuric acid
O=C1O[C@H]([C@@H](O)CO)C(O)=C1O
L-ascorbic acid
→
CC1(C)OCC(C2OC(=O)C(O)=C2O)O1
5,6-O-isopropylidene-L-ascorbic acid
Yield 115.4%

Reactants

CC(C)=O
acetone
O=S(=O)(O)O
sulfuric acid
O=C1O[C@H]([C@@H](O)CO)C(O)=C1O
L-ascorbic acid

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe mixture was then reacted at the temperature of the previous step for 17 hours
  2. 2
    Filtrationfiltered
  3. 3
    Washwashed with cold acetone

Procedure

With nitrogen substitution, 557.8 grams (9.6 moles) of acetone was cooled to −5 degrees C., 54.3 grams (0.2 moles) of 28% fuming sulfuric acid was dripped, and 176.1 grams (1.0 mole) of L-ascorbic acid was added. The mixture was then reacted at the temperature of the previous step for 17 hours, filtered and washed with cold acetone to obtain 249.5 grams of 5,6-O-isopropylidene-L-ascorbic acid (86.7% in purity) in the form of a wet cake.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07569211B2uspto-grants-2009_08