Isopropanol → Dodecyl propan-2-yl hydrogen phosphate

HRID 441369Notes

Reaction equation

HRID 441369 reaction equation
[CH2:1]([OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH:14]([OH:17])([CH3:16])[CH3:15].[O:18]=[P:19]12OP3(OP(OP(O3)(O1)=O)(=O)[O:20]2)=O>CCCCCC>[P:19]([OH:20])([O:17][CH:14]([CH3:16])[CH3:15])([O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:18]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 81931-DodecanolHCID 14812Phosphorus oxide (P4O10)

Product 1

HCID 21420852Dodecyl propan-2-yl hydrogen phosphate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Dodecyl isopropyl hydrogen phosphate was prepared by slowly adding a mixture of 0.2 g. mole each of 1-dodecanol and isopropyl alcohol to a stirred slurry of 0.1 g. mole of P2O5 in 100 ml. hexane, holding the temperature of the reaction mixture below its boiling point by use of a water bath. After the addition was complete, stirring was continued until the mixture was clear and then the hexane was distilled off, the last portion under reduced pressure. The product was a clear, colorless liquid which crystallized slowly into a waxy, white solid. It was primarily the desired mixed ester with small amounts of the two symmetrical diesters.

Workup

  1. additionby slowly adding
  2. additiona mixture of 0.2 g
  3. additionAfter the addition
  4. distillationthe hexane was distilled off
  5. customcrystallized slowly into a waxy, white solid
  6. additiondesired mixed ester with small amounts of the two symmetrical diesters

Sources & evidence

ORD record
ord-83a3f0591fb845038b09d208a5907148
Source dataset
uspto-grants-1977_08
Patent number
US04039636

Reaction notes

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