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Tributylphosphine → HCID 68419400, compound

HRID 2356168
Notes
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Reaction equation

HRID 2356168 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

To 350 mL of dehydrated methylene chloride, 12.8 g (66 mmol) of 2-hexyloxyphenol, 23.3 g (73 mmol) of 16-bromohexadecane-1-ol, and 20.0 g (99 mmol) of tri-n-butylphosphine were added. The resulting mixture was cooled with ice under argon. After 25.0 g (99 mmol) of 1,1′-(azodicarbonyl)dipiperidine was added bit by bit while stirring the mixture, 150 mL of methylene chloride was added. Under argon, the mixture was stirred at ambient temperature for 30 minutes and was refluxed for 6 hours. After being cooled, the reaction solution was put into 100 mL of hexane and was filtered. The filtered liquid was purified by silica-gel column chromatography. As a result, 26.5 g of a transparent liquid was obtained.

Workup

  1. temperatureThe resulting mixture was cooled with ice under argon
  2. additionwas added
  3. temperaturewas refluxed for 6 hours
  4. temperatureAfter being cooled
  5. filtrationwas filtered
  6. customThe filtered liquid was purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-846ddec337684784ae02943f5369d82c
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07758932B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes