Sodium Chloride → 2,4-Hexadiyn-1,6-diol bis(p-methoxybenzene sulfonate)

HRID 903545

Reaction equation

HRID 903545 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH2:13]([OH:20])[C:14]#[C:15][C:16]#[C:17][CH2:18][OH:19].[OH-:21].[K+].[Cl-].[Na+]>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:19][CH2:18][C:17]#[C:16][C:15]#[C:14][CH2:13][O:20][S:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:10])=[O:21])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 74014-Methoxybenzenesulfonyl chlorideHCID 14797Potassium Hydroxide2×HCID 94973Diacetylene glycol

Product 1

HCID 186282212,4-Hexadiyn-1,6-diol bis(p-methoxybenzene sulfonate)Yield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Fifty grams of p-methoxybenzenesulfonyl chloride was reacted, at 15° to 18° C., with 11 grams of 2,4-hexadiyn-1,6-diol in 100 ml tetrahydrofuran, while a solution of 20 grams potassium hydroxide in 180 ml water was added dropwise over a 10 minute period. The resulting exothermic reaction was cooled at 15° to 18° C. with the aid of an ice-water bath. After the addition of the potassium hydroxide solution, the solution was allowed to stir overnight at room temperature. The mixture was then poured into 500 ml cold aqueous sodium chloride solution which resulted in a yellow precipitate. The precipitate was collected by filtration, washed with water and dried. Obtained was 41.6 grams (93% yield of theory) of a yellow brown solid, melting point 120° to 122° C.

Workup

  1. additionwas added dropwise over a 10 minute period
  2. customThe resulting exothermic reaction
  3. temperaturewas cooled at 15° to 18° C. with the aid of an ice-water bath
  4. customresulted in a yellow precipitate
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water
  7. customdried
  8. customObtained

Sources & evidence

ORD record
ord-e2e002cfcdfe4caa8f00335a0f59b455
Source dataset
uspto-grants-1980_10
Patent number
US04228126

Linked notes

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