Water → HCID 69492718, compound

HRID 1275428Notes

Reaction equation

HRID 1275428 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].[OH-].[K+].O>ClCCl>[CH3:12][O:13][CH:14]([S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][OH:22]

Participants

6

Reactant 4

HCID 962Water2×HCID 73974-Toluenesulfonyl chlorideHCID 8178Triethylene glycol monomethyl etherHCID 14797Potassium Hydroxide

Product 1

HCID 69492718HCID 69492718, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

200 g of p-toluenesulfonyl chloride and 172.4 g of triethylene glycol monomethyl ether are dissolved in 1 liter of dichloromethane and cooled to 0° C. With vigorous stirring, 236.3 g of freshly powdered potassium hydroxide are metered in at a rate such that the temperature does not exceed 5° C. The mixture is maintained at 0° C. for 3 hours. 1 liter of dichloromethane and 1.2 liters of iced water are added. If more solids form, a further 0.5 liter of iced water are added. The organic phase is separated off and washed with 0.3 liter of saturated sodium chloride solution. It is dried over Na2SO4 and evaporated to dryness under reduced pressure.

Workup

  1. customdoes not exceed 5° C
  2. temperatureThe mixture is maintained at 0° C. for 3 hours
  3. customThe organic phase is separated off
  4. washwashed with 0.3 liter of saturated sodium chloride solution
  5. dry with materialIt is dried over Na2SO4
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8a2b161fa12342b5b8c49460267bf311
Source dataset
uspto-grants-2000_12
Patent number
US06160180

Reaction notes

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