Isopropanol → trans 4-(Bromomethyl)-2-isopropoxy-1,3-dioxolane
Reaction equation
[Br:1][CH2:2][C@@H:3]1[CH2:7][O:6][C@@H:5]([O:8]C)[O:4]1.C(O)(C)C.[C:14]1([CH3:24])[CH:19]=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][CH2:2][C@@H:3]1[CH2:7][O:6][C@@H:5]([O:8][CH:14]([CH3:19])[CH3:24])[O:4]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of cis and trans 4-(bromomethyl)-2-methoxy-1,3-dioxolane (example 1) (5.37 g, 27.3 mmol) in benzene (100 mL) was added isopropanol (2.2 mL, 28.6 mmol, 1.05 eq.) and p-toluenesulfonic acid (pTSA, few crystals). The mixture was stirred for 24 hr at 88°-90° C. followed by addition of isopropanol (0.5 mL, 0.24 eq.). The mixture was stirred for further 24 hr at 90° C., cooled to room temperature and benzene was removed under reduced pressure. The crude material was obtained in quantitative yield consisting of a mixture of isopropoxy and methoxy orthoesters in a 9:1 ratio respectively. The ratio of cis and trans isomers was about 1:1.
Workup
- stirringThe mixture was stirred for further 24 hr at 90° C.
- custombenzene was removed under reduced pressure
Sources & evidence
- ORD record
- ord-7db678d5023043d184562e8ec2f882a1
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05955610
Reaction notes
Loading…