p-Toluenesulfonic acid → trans 4-(Bromomethyl)-2-methoxy-1,3-dioxolane
Reaction equation
[Br:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].[CH3:7][O:8][CH:9](OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][CH2:2][C@@H:3]1[CH2:4][O:5][C@@H:7]([O:8][CH3:9])[O:6]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-bromo-1,2-propanediol (6.0 g, 38.7 mmol) in benzene (90 mL) was added trimethylorthoformate (4.23 mL, 38.7 mmol, 1 eq.) and p-toluenesulfonic acid (pTSA, few crystals). The mixture was stirred for 20 hr at 85°-90° C., then cooled to room temperature and benzene was removed under reduced pressure. The crude material was obtained in 96% yield (7.26 g) as a mixture of cis and trans isomers in a 1:1 ratio.
Workup
- custombenzene was removed under reduced pressure
Sources & evidence
- ORD record
- ord-b1552334a7ac4abf8a0b3a375d1f32e8
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06127540
Reaction notes
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