p-Toluenesulfonic acid → trans 4-(Bromomethyl)-2-methoxy-1,3-dioxolane

HRID 618828Notes

Reaction equation

HRID 618828 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]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 208273-Bromo-1,2-propanediol

Product 1

HCID 86752979trans 4-(Bromomethyl)-2-methoxy-1,3-dioxolaneYield 96%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

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

  1. custombenzene was removed under reduced pressure

Sources & evidence

ORD record
ord-1f567559ecbb4e8f8ce72dcc4267cf0d
Source dataset
uspto-grants-1999_09
Patent number
US05955610

Reaction notes

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