3-Chloro-1,2-propanediol → HCID 86748628, compound

HRID 1654427Notes

Reaction equation

HRID 1654427 reaction equation
[OH-].[Na+].[CH2:3]([SH:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].Cl[CH2:13][CH:14]([OH:17])[CH2:15][OH:16]>C(O)(C)C>[CH2:3]([S:11][CH2:13][CH2:14][CH2:15][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH:16][CH2:15][CH:14]([OH:17])[CH3:13]

Participants

5

Reactant 3

HCID 72903-Chloro-1,2-propanediolHCID 81441-OctanethiolHCID 14798Sodium Hydroxide

Product 1

HCID 86748628HCID 86748628, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

Approximately 40 g of 50% aqueous sodium hydroxide solution was added dropwise over a period of 1 hour to a solution of n-octyl mercaptan (72.3 g) and 1-chloropropane-2,3-diol (55 g) in isopropanol solvent (400 cc) at ambient temperature. The reaction temperature rose from 23° to 55° C. during addition. The reaction was refluxed for 3 hours at 80° C. and then filtered hot through paper to remove the precipitated salts. The isopropanol solvent was removed by distillation. The product residue was dissolved in 700 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 colorless, opaque fluid.

Workup

  1. additionThe reaction temperature rose from 23° to 55° C. during addition
  2. filtrationfiltered hot through paper
  3. customto remove the precipitated salts
  4. customThe isopropanol solvent was removed by distillation
  5. dissolutionThe product residue was dissolved in 700 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 colorless, opaque fluid

Sources & evidence

ORD record
ord-628ee65c9e1d4531a61d5db1b1ce06d4
Source dataset
uspto-grants-1995_04
Patent number
US05407451

Reaction notes

Loading…