Isopropanol → Diisopropyl tartrate

HRID 2289168Notes

Reaction equation

HRID 2289168 reaction equation
[C:1]([OH:10])(=[O:9])[C@@H:2]([C@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].[CH:11](O)([CH3:13])[CH3:12].[CH3:15][C:16]1C=CC(S(O)(=O)=O)=C[CH:21]=1>C1C=CC=CC=1>[C:6]([C@@H:4]([C@H:2]([C:1]([O:10][CH:16]([CH3:21])[CH3:15])=[O:9])[OH:3])[OH:5])([O:8][CH:11]([CH3:13])[CH3:12])=[O:7]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 6101p-Toluenesulfonic acidHCID 444305L-Tartaric acid

Product 1

HCID 6453580Diisopropyl tartrate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Diisopropyl (R,R)-tartrate was prepared according to the procedure described in J. Am. Chem. Soc., 1981, 6237. 400 g of (R,R)-tartaric acid, 400 mL of isopropanol and 5 g of p-TsOH were heated in refluxing benzene to afford, following distillation, 201 g (55%) of the above-titled compound: bp.=103-105° C. (2 torr) (lit. 152° C. (12 torr)).

Workup

  1. customto afford
  2. distillationdistillation, 201 g (55%) of the above-titled compound
  3. custombp.=103-105° C. (2 torr) (lit. 152° C. (12 torr))

Sources & evidence

ORD record
ord-3e40acb0fd9d4c72a1af656056f49efb
Source dataset
uspto-grants-2000_07
Patent number
US06090950

Reaction notes

Loading…