Triethylamine → O-(+)-menthyl dichlorophosphate

HRID 1741801

Reaction equation

HRID 1741801 reaction equation
[CH3:1][C@@H:2]1[CH2:7][C@H:6]([OH:8])[C@@H:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1.C(N(CC)CC)C.[O:19]=[P:20](Cl)([Cl:22])[Cl:21]>C1(C)C=CC=CC=1>[P:20]([Cl:22])([Cl:21])([O:8][CH:6]1[CH:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3][CH:2]([CH3:1])[CH2:7]1)=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 165675(+)-Menthol

Product 1

HCID 12473339O-(+)-menthyl dichlorophosphateYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 7.5 g (48 mmol) of (1S, 2R, 5S)-(+)-menthol (Aldrich) and 4.86 g (48 mmol) of triethylamine in 20 ml of toluene was dropped into 7.36 g (48 mmol) of POCl3 at 0° C. The entire solution was stirred for 23 hours at room temperature. The insoluble triethylamine hydrochloride was filtered and the solvent was evaporated. Yield 99%, 31P NMR δ 6.76 (CDCl3). (lit. T. Milobedzki, W. Janczak, Roczniki Chemji 11, 840 (1931)).

Workup

  1. filtrationThe insoluble triethylamine hydrochloride was filtered
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1fad478ae6fa49e19328d42f2e875834
Source dataset
uspto-grants-1994_08
Patent number
US05334741

Linked notes

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