3-Chloro-1,2-propanediol → 1,2-Dihydroxypropane dodecyl sulfide

HRID 1654425Notes

Reaction equation

HRID 1654425 reaction equation
[OH-].[Na+].[CH2:3]([SH:15])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].Cl[CH2:17][CH:18]([OH:21])[CH2:19][OH:20]>C(O)(C)C>[CH2:3]([S:15][CH2:17][CH2:18][CH2:19][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[OH:20][CH2:19][CH:18]([OH:21])[CH3:17]

Participants

5

Reactant 3

HCID 72903-Chloro-1,2-propanediolHCID 81951-DodecanethiolHCID 14798Sodium Hydroxide

Product 1

HCID 867397751,2-Dihydroxypropane dodecyl sulfide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

Approximately 97 g of 50% aqueous sodium hydroxide solution was added dropwise over a period of 7 hours to a solution of n-dodecyl mercaptan (1000 g) and 1-chloropropane-2,3-diol (547 g) in isopropanol solvent (2000 cc) at ambient temperature. The reaction temperature rose from 21° to 56° C. during the addition. The reaction was refluxed for 5 hours at 80° C. and then filtered hot through paper to remove the precipitated salt. The isopropanol solvent was removed by distillation. The product residue was dissolved in about 4000 cc of toluene and washed with water several times. The toluene solution was dried over magnesium sulfate and filtered through diatomaceous earth. Toluene was removed by high speed rotary evaporation under reduced pressure to yield a white solid product.

Workup

  1. additionThe reaction temperature rose from 21° to 56° C. during the addition
  2. filtrationfiltered hot through paper
  3. customto remove the precipitated salt
  4. customThe isopropanol solvent was removed by distillation
  5. dissolutionThe product residue was dissolved in about 4000 cc of toluene
  6. washwashed with water several times
  7. dry with materialThe toluene solution was dried over magnesium sulfate
  8. filtrationfiltered through diatomaceous earth
  9. customToluene was removed by high speed rotary evaporation under reduced pressure
  10. customto yield a white solid product

Sources & evidence

ORD record
ord-f9be3fbf01ef42c395a74006935bf358
Source dataset
uspto-grants-1995_04
Patent number
US05407451

Reaction notes

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