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

HRID 537606
Notes
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Reaction equation

HRID 537606 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-142829e8ee0c4fef8af04aabfe9c94f4
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08859732B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes