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Imidazole → 1-[3-Iodo-2,2-bis(octadecyloxymethyl)propoxy]octadecane

HRID 1502535
Notes
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Reaction equation

HRID 1502535 reaction equation
[CH2:1]([O:19][CH2:20][C:21]([CH2:44][O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])([CH2:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:22]O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:88]I>C1(C)C=CC=CC=1>[I:88][CH2:22][C:21]([CH2:44][O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])([CH2:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:20][O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 142519643-(Octadecyloxy)-2,2-bis[(octadecyloxy)methyl]-1-propanol

Product 1

HCID 594992271-[3-Iodo-2,2-bis(octadecyloxymethyl)propoxy]octadecaneYield 98.8%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent
2×

Conditions

Temperature
100 °C

Procedure

2,2,2-Tris(octadecyloxymethyl)ethanol (500 mg, 560 μmol) was dissolved in toluene (10 ml), triphenylphosphine (294 mg, 1.12 mmol), imidazole (76.2 mg, 1.12 mmol) and iodine (284 mg, 1.12 mmol) were added, and the mixture was stirred at 100° C. overnight. The reaction mixture was cooled to room temperature, toluene (10 ml) was added, and the mixture was partitioned and washed three times with water (5 ml). The organic layer was evaporated under reduced pressure, and the residue was precipitated with acetonitrile (10 ml) to give 1-[3-iodo-2,2-bis(octadecyloxymethyl)propoxy]octadecane (555 mg, 553 μmol, yield 98%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe mixture was partitioned
  3. washwashed three times with water (5 ml)
  4. customThe organic layer was evaporated under reduced pressure
  5. customthe residue was precipitated with acetonitrile (10 ml)

Sources & evidence

ORD record
ord-564e7d2faa0f48d9a365e10b029c419b
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09206230B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes