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

HRID 865781Notes

Reaction equation

HRID 865781 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.[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][OH:22]>N1C=CC=CC=1>[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 8178Triethylene glycol monomethyl ether

Product 1

HCID 99488982-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 22 was prepared using the method described for the synthesis of compound 18. The reagents used were as follows, p-toluene sulphonyl chloride (170.4 g, 0.894 mol.), pyridine (400 ml) and 2-(2'-(2"-methoxy ethoxy)ethoxy)ethanol (148.7 g, 0.907 mol.) (Aldrich). The final product was a pale yellow liquid (122 g, 42%): 1H-NMR (CDCl3), d (ppm) 7.3-7.7 (m, 4H aromatic), 3.3-4.2 (m, 12H) 3.35 (s, 3H), 2.4 (s, 3H). Mass spectroscopy, m/e: 318 M+.

Workup

  1. customCompound 22 was prepared

Sources & evidence

ORD record
ord-510191d889af40c89775b6a46679b3f5
Source dataset
uspto-grants-1996_10
Patent number
US05567783

Reaction notes

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