HCID 68969962, compound → HCID 24830904, compound

HRID 2410621Notes

Reaction equation

HRID 2410621 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][P:22](=[O:25])([OH:24])[OH:23])C1C=CC=CC=1>CO>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][P:22](=[O:23])([OH:24])[OH:25]

Participants

3

Reactant 1

HCID 68969962HCID 68969962, compound

Product 1

HCID 24830904HCID 24830904, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a single-neck flask with a reflux condenser, 12-diethoxyphosphoryl benzoate (4.0 g, 9.3 mmol) is weighed and concentrated HCl (10 mL) is added. The mixture is brought to a temperature of 100° C. and left stirring under a static head of nitrogen. After 72 hours ethyl acetate (80 mL) and distilled water (40 mL) are added. Separation is carried out in a separating funnel and the water is extracted three more times with ethyl acetate (3×50 mL). The combined organic phases are washed with a saturated solution of NaCl, anhydrified with anhydrous sodium sulphate and concentrated in the Rotavapor and in the high vacuum pump. Column chromatography is performed on silica gel with eluant petroleum ether/ethyl acetate 1/1. The benzoic acid subproduct is isolated first and then, after changing to pure methanol as eluant, the product 12-benzyloxydodecyl phosphoric acid. Continuing column chromatography, the total hydrolysis product 12-hydroxydodecyl phosphoric acid is also isolated. The last two products (about 2.0 g) are kept together and used in the next stage.

Sources & evidence

ORD record
ord-adf06895b3de4a24873f852f1d48926b
Source dataset
uspto-grants-2014_08
Patent number
US08816107B2

Reaction notes

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