4-Toluenesulfonyl chloride → 2-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

HRID 881036Notes

Reaction equation

[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH-].[Na+].[CH3:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][OH:24]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl.O>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16][O:15][CH3:14])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 12.5 °C

Procedure

A 300 gallon glass lined reactor was charged with p-toluene sulfonyl chloride (2) and methylene chloride. A second 300 gallon glass lined reactor was charged with USP water, sodium hydroxide, methylene chloride, triethyleneglycol monomethyl ether (TEG) (1), and benzyltriethyl ammonium chloride. The p-toluene sulfonyl chloride solution was slowly added over 2 hours to the TEG solution while maintaining a temperature of 0-25° C. The reaction mixture was agitated for 1 hour and sampled for reaction completion analysis by HPLC. The product was isolated by separating the methylene chloride layer (product layer) from the aqueous layer. The organic layer was washed twice with water and the methylene chloride was replaced with toluene by vacuum distillation to yield 2-(2-(2-methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (Ts-TEG) (3).

Workup

aliquotsampled for reaction completion analysis by HPLC
customThe product was isolated
customby separating the methylene chloride layer (product layer) from the aqueous layer
washThe organic layer was washed twice with water
distillationthe methylene chloride was replaced with toluene by vacuum distillation

Sources & evidence

ORD record: ord-a4a2d0435d97482a99c0bbe846451e71
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993606B2

Reaction notes

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