Triethyl phosphite → HCID 18462421, compound

HRID 2304132Notes

Reaction equation

Br[CH2:2][CH2:3][CH:4]([CH3:21])[CH2:5][CH2:6][CH2:7][CH:8]([CH3:20])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:19])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17].[P:22]([O:29]CC)([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25]>>[CH2:24]([O:23][P:22]([CH2:2][CH2:3][CH:4]([CH3:21])[CH2:5][CH2:6][CH2:7][CH:8]([CH3:20])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:19])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])([O:26][CH2:27][CH3:28])=[O:29])[CH3:25]

Participants

Reactant 2

HCID 31215Triethyl phosphite2×

HCID 10808570Phytanyl Bromide

Product 1

HCID 18462421HCID 18462421, compoundYield 94%

Conditions

Temperature: 150 °C

Procedure

A mixture of 21.69 g (60 mmol) of 1-bromo-3,7,11,15-tetramethylhexadecane and 25 g (150 mmol) of triethyl phosphite was heated at 150° C. After 18 h, an additional 20 g (120 mmol) of triethyl phosphite was added, and heating was continued for 24 h. Diethyl ethylphosphonate and other volatiles were distilled, bp 30-50° C. at 0.05 mm Hg, and bulb-to-bulb distillation of the concentrate provided 23.51 g (94%) of 1-(diethylphosphono)-3,7,11,15-tetramethylhexadecane as a clear, colorless liquid, bp 190-230° C. at 0.05 mm Hg.

Workup

temperatureheating
waitwas continued for 24 h
distillationDiethyl ethylphosphonate and other volatiles were distilled
distillationbp 30-50° C. at 0.05 mm Hg, and bulb-to-bulb distillation of the concentrate

Sources & evidence

ORD record: ord-e98eb7e152fe4d7295a89df258f42c10
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06433359B1

Reaction notes

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