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Tributylphosphine → HCID 68419400, compound

HRID 1442477
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Reaction equation

HRID 1442477 reaction equation
[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Br:15][CH2:16][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]O.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>CCCCCC.C(Cl)Cl>[Br:15][CH2:16][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][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 275701316-Bromo-1-hexadecanolHCID 124137162-(Hexyloxy)phenol

Product 1

HCID 68419400HCID 68419400, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
2×
HCID 8058HexaneSolvent

Procedure

12.8 g (66 mmol) of 2-hexyloxyphenol, 23.3 g (73 mmol) of 16-bromohexadecan-1-ol and 20.0 g (99 mmol) of tri-n-butylphosphine were added to 350 mL of dehydrated methylene chloride followed by cooling with ice in the presence of argon. After adding 25.0 g (99 mmol) of 1,1′-(azodicarbonyl) dipiperidine a little at a time while stirring, 150 mL of methylene chloride were added. After stirring for 30 minutes at room temperature in the presence of argon, the reaction solution was refluxed for 6 hours. After cooling, the reaction solution was dropped into 100 mL of hexane and filtered. The filtrate was concentrated and purified by silica gel column chromatography to obtain 26.5 g of a clear liquid.

Workup

  1. temperatureby cooling with ice in the presence of argon
  2. stirringAfter stirring for 30 minutes at room temperature in the presence of argon
  3. temperaturethe reaction solution was refluxed for 6 hours
  4. temperatureAfter cooling
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-a9a844d735ff48ecbe1a10a69da6dc70
Source dataset
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07658979B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes