Benzyl Alcohol → HCID 58903108, compound

HRID 273372Notes

Reaction equation

HRID 273372 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH:11]=1.[CH2:24](O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[CH2:24]([O:8][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][O:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)[CH:11]=2)=[C:4]([CH3:9])[CH:5]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 58903178HCID 58903178, compound

Product 1

HCID 58903108HCID 58903108, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

A solution of 2,6-dimethyl-3′-[(tetrahydro-2H-pyran-2-yloxy)methyl]biphenyl-4-ol (1.78 g, 5.70 mmol), benzyl alcohol (0.885 mL, 8.55 mmol) and tributylphosphine (2.13 mL, 8.55 mmol) in toluene (80 mL) was stirred under ice-cooling, and 1,1′-(azodicarbonyl)dipiperidine (2.16 g, 8.55 mmol) was added by small portions. The mixture was warmed to room temperature and stirred for 24 hrs. Hexane (40 mL) was added to the reaction mixture and the precipitated insoluble material was filtered off. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-10% ethyl acetate/hexane) to give the title compound as a colorless oil (1.71 g, yield 75%).

Workup

  1. temperaturecooling
  2. filtrationthe precipitated insoluble material was filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a81052de40b14a569d77fc15c54ec2b7
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

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