Triethylamine → S-ethyl S-hexyl O-(3-formylmethylphenyl) dithiophosphate

HRID 1105584Notes

Reaction equation

HRID 1105584 reaction equation
[P:1](Cl)([S:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])([S:3][CH2:4][CH3:5])=[O:2].C(N(CC)CC)C.[OH:21][C:22]1[CH:23]=[C:24]([CH2:28][CH:29]=[O:30])[CH:25]=[CH:26][CH:27]=1>C(Cl)Cl>[P:1]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH:29]=[O:30])[CH:23]=1)([S:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])([S:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 149952072-(3-Hydroxyphenyl)acetaldehydeHCID 86738193S-ethyl S-hexyl chlorodithiophosphate

Product 1

HCID 86738192S-ethyl S-hexyl O-(3-formylmethylphenyl) dithiophosphate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of S-ethyl S-hexyl chlorodithiophosphate (0.03 mole) in methylene chloride (50 ml) is charged into a glass reaction vessel equipped with a mechanical stirrer. Triethylamine (0.03 mole) is added and the mixture is cooled to a temperature of about 0° C. A solution of 3-hydroxylphenylacetaldehyde (0.03 mole) in methylene chloride (15 ml) is slowly added with stirring while maintaining the temperature of the reaction mixture at about 0° C. After the addition is completed, the reaction mixture is allowed to warm to room temperature and stirring is continued for a period of about 1 hour. After this time the reaction mixture is transferred to a separatory funnel and methylene chloride (100 ml) is added. The resulting solution is then washed with water, dilute aqueous sodium hydroxide and again with water. The washed solution is dried over anhydrous magnesium sulfate, is filtered and stripped of solvent under vacuum to yield the desired product S-ethyl S-hexyl O-(3-formylmethylphenyl) dithiophosphate.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturewhile maintaining the temperature of the reaction mixture at about 0° C
  3. additionAfter the addition
  4. temperatureto warm to room temperature
  5. stirringstirring
  6. customAfter this time the reaction mixture is transferred to a separatory funnel
  7. washThe resulting solution is then washed with water, dilute aqueous sodium hydroxide and again with water
  8. dry with materialThe washed solution is dried over anhydrous magnesium sulfate
  9. filtrationis filtered

Sources & evidence

ORD record
ord-cd5744d3d2aa44afb5c5def9cfb78ba6
Source dataset
uspto-grants-1982_01
Patent number
US04309422

Reaction notes

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