Hydrochloric Acid → 2-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

HRID 566834

Reaction equation

HRID 566834 reaction equation
[OH-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][OH:13].[S:14](Cl)([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15].Cl>C1COCC1.O>[S:14]([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)([O:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH3:3])(=[O:16])=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8178Triethylene glycol monomethyl etherHCID 14798Sodium Hydroxide

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

In an oven dried 12 L three-necked roundbottom flask, equipped with a magnetic stir bar and a 1000 mL pressure-equalizing dropping funnel, a solution of NaOH (440.0 g, 11.0 mol) is added to 1800 mL water and the mixture is cooled to approximately 0° C. A solution of triethylene glycol monomethyl ether, Formula A, (656.84 g, 4.0 mol) in THF (1000 mL) is added. The clear solution is stirred vigorously at 0° C. for 15 min and a solution of tosyl chloride (915.12, 4.8 mol) in THF (2.0 L) added dropwise over a 1 h period. The reaction mixture is stirred for an additional 1 h at 0° C., and 10% HCl (5.0 L) is added to quench the reaction (to pH 5-7). The two-phase mixture is transferred to a 4 L separatory funnel, the organic layer removed, and the aqueous layer extracted with t-butylmethyl ether (3×250 mL). The combined organic extracts are washed with brine (2×350 mL), dried (MgSO4), and evaporated under reduced pressure to afford Formula B, 1217.6 g (95%) as a light colored oil. This material is taken to the next step without further purification.

Workup

  1. customIn an oven dried 12 L three-necked roundbottom flask
  2. customequipped with a magnetic stir bar
  3. stirringThe reaction mixture is stirred for an additional 1 h at 0° C.
  4. customto quench
  5. customthe reaction (to pH 5-7)
  6. customThe two-phase mixture is transferred to a 4 L separatory funnel
  7. customthe organic layer removed
  8. extractionthe aqueous layer extracted with t-butylmethyl ether (3×250 mL)
  9. washThe combined organic extracts are washed with brine (2×350 mL)
  10. dry with materialdried (MgSO4)
  11. customevaporated under reduced pressure
  12. customto afford Formula B, 1217.6 g (95%) as a light colored oil
  13. customThis material is taken to the next step without further purification

Sources & evidence

ORD record
ord-eaddb5bed32e4afea18f9c1f10b67ebd
Source dataset
uspto-grants-2001_01
Patent number
US06176842B1

Linked notes

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