Stearyl Alcohol → HCID 19742177, compound

HRID 2255344Notes

Reaction equation

HRID 2255344 reaction equation
[CH2:1]([N:5]1[C:9]2([CH2:14][O:13][P:12](Cl)[O:11][CH2:10]2)[CH2:8][O:7][P:6]1Cl)[CH:2]([CH3:4])[CH3:3].[CH2:17]([OH:35])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].C(N([CH2:41][CH3:42])CC)C>C1(C)C=CC=CC=1>[CH2:1]([N:5]1[C:9]2([CH2:14][O:13][P:12]([O:35][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[O:11][CH2:10]2)[CH2:8][O:7][P:6]1[O:35][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:41][CH3:42])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8221Stearyl AlcoholHCID 8471TriethylamineHCID 19742171HCID 19742171, compound2×

Product 1

HCID 19742177HCID 19742177, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

The procedure of Example 10 is repeated using 10.89 g (36 mmol) of 1-isobutyl-2,8-dichloro-3,7,9-trioxa-1aza-2,8-diphosphaspiro[4.5]decane (compound of Example 8) in 200 mL of toluene and 19.25 g (77 mmol) of n-octadecanol and 7.92 g (10.9 mL, 78 mmol) of triethylamine in 100 mL of toluene to give 26.34 g of white solid. The residue is purified by flash chromatography (basic alumina, 3% ethyl acetate/97% hexane) to give 9.23 g (34% yield) of a white solid melting at 33°-39° C. The product is identified by mass spectroscopy: m/z=773.

Sources & evidence

ORD record
ord-b6d052610b4d4180a13de6b8c5c8f526
Source dataset
uspto-grants-1993_08
Patent number
US05239103

Reaction notes

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