Benzyl Alcohol → HCID 20432988, compound

HRID 2412358Notes

Reaction equation

HRID 2412358 reaction equation
[CH2:1]([S:19][CH2:20][CH2:21][CH2:22]Cl)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]CCCCCC.[NH:24]([CH2:28][CH2:29][OH:30])[CH2:25][CH2:26][OH:27].C(O)C1C=CC=CC=1.[OH-].[Na+]>>[CH2:1]([S:19][CH2:20][CH2:21][CH2:22][N:24]([CH2:28][CH2:29][OH:30])[CH2:25][CH2:26][OH:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 4

HCID 244Benzyl AlcoholHCID 8113DiethanolamineHCID 14798Sodium HydroxideHCID 20432998HCID 20432998, compound

Product 1

HCID 20432988HCID 20432988, compound

Procedure

A mixture of 3-octadecylthiopropyl chloride (3.53 g., 0.01 mole), diethanolamine (2.1 g., 0.02 mole) and benzyl alcohol (5 ml.) is heated under reflux for one-half hour, then treated with an ethanolic solution of sodium hydroxide (0.4 g., 0.01 mole) and refluxed for five more minutes. The mixture is cooled, filtered, and the ethanol removed by evaporation. The benzyl alcohol is then removed by distillation in vacuo and the residue chromatographed on silica using first ether then methanol as eluants. The desired product is contained in the methanol eluate. It is isolated by evaporation of the solvent, m.p. 53°-54° C. Its hydrochloride salt melts at 65°-66° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for one-half hour
  3. temperaturerefluxed for five more minutes
  4. temperatureThe mixture is cooled
  5. filtrationfiltered
  6. customthe ethanol removed by evaporation
  7. customThe benzyl alcohol is then removed by distillation in vacuo
  8. customthe residue chromatographed on silica using first ether
  9. customIt is isolated by evaporation of the solvent, m.p. 53°-54° C

Sources & evidence

ORD record
ord-87c471e483f14d49bf170be2cf6d5f72
Source dataset
uspto-grants-1985_01
Patent number
US04491583

Reaction notes

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