2-Methyltetrahydrofuran → Benzenesulfonic Acid

HRID 467843Notes

Reaction equation

HRID 467843 reaction equation
CC1CCCO1.O.[C:8]1([S:14]([OH:17])(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(OC(C)C)(=O)C>[C:8]1([S:14]([OH:17])(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 73012-MethyltetrahydrofuranHCID 15619088Hydroxybenzenesulfonic acid

Product 1

HCID 7371Benzenesulfonic Acid

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent

Procedure

15.0 g of Compound 1 and 120 ml 2-methyltetrahydrofuran were charged to reactor A. 7.25 g benzenesulfonic acid hydrate and 180 ml isopropyl acetate was charged to reactor B. Reactor B contents were dried via zoetrope (solvent swap with fresh isopropyl acetate) twice to provide a dry solution of benzenesulfonic acid in isopropyl acetate. Reactor B contents were charged into reactor A at ambient temperature. The resulting slurry was heated to reflux (homogeneous solution attained), and then cooled immediately to ambient temperature to afford a slurry. The slurry was concentrated under reduced pressure to ½ volume, followed by addition of isopropyl acetate to achieve the original volume. The concentration and suspension in isopropyl acetate was repeated followed by concentration to ½ volume, filtration, and a washed with isopropyl acetate. The cake was dried in a vacuum oven at 50° C. to provide Form XIV.

Workup

  1. dry with materialReactor B contents were dried via zoetrope (solvent swap with fresh isopropyl acetate) twice

Sources & evidence

ORD record
ord-f51ea84807964917b8bf6bb3e5f343ed
Source dataset
uspto-grants-2014_01
Patent number
US08623894B2

Reaction notes

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