Triphenylphosphine → HCID 20034926, compound

HRID 231252

Reaction equation

HRID 231252 reaction equation
[OH:1][CH2:2][C:3]1([CH3:10])[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9].O[C:12]1[CH:20]=[CH:19][C:15]([CH2:16][C:17]#[N:18])=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1C=CC=CC=1.[OH-].[Na+]>[CH3:10][C:3]1([CH2:2][O:1][C:12]2[CH:20]=[CH:19][C:15]([CH2:16][C:17]#[N:18])=[CH:14][CH:13]=2)[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 265484-Hydroxybenzyl cyanideHCID 5462977Diethyl azodicarboxylateHCID 113555322-Hydroxymethyl-2-methylcyclohexanone

Product 1

HCID 20034926HCID 20034926, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-Hydroxymethyl-2-methylcyclohexanone [Pearson et al., J. Chem. Soc. Perkin I, 2774, 2778 (1980)] (3.7 g), 4-hydroxybenzyl cyanide (4.49 g) and triphenylphosphine (8.86 g) were dissolved in benzene (100 mL) and cooled in ice under a nitrogen atmosphere. Diethylazodicarboxylate (5.3 mL) was added dropwise and the mixture was allowed to warm to room temperature. The reaction was then refluxed overnight. After cooling to room temperature, the reaction mixture was diluted with 25% aqueous NaOH and extracted with benzene. The extracts were washed with saturated brine solution, dried over MgSO4, filtered and concentrated. The crude residue was chromatographed on SiO2, elution with dichloromethane to give 4.35 g (65% yield) of 2-methyl-2-[[4-(cyanomethyl)phenoxy]methyl]cyclohexanone as an amber oil.

Workup

  1. temperaturecooled in ice under a nitrogen atmosphere
  2. temperatureThe reaction was then refluxed overnight
  3. temperatureAfter cooling to room temperature
  4. extractionextracted with benzene
  5. washThe extracts were washed with saturated brine solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue was chromatographed on SiO2, elution with dichloromethane

Sources & evidence

ORD record
ord-b270ecb836b944b4b0260c814845aa6b
Source dataset
uspto-grants-1989_07
Patent number
US04845231

Linked notes

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