P-Cresol → HCID 19915363, compound

HRID 1090456Notes

Reaction equation

HRID 1090456 reaction equation
[F:1][C:2]([F:15])=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14].[CH3:16][C:17]1[CH:22]=[CH:21][C:20](O)=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[C:2]([F:15])[F:1])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 2879P-CresolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1181687611-Dodecen-1-ol, 12,12-difluoro-

Product 1

HCID 19915363HCID 19915363, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.0 gram (0.0045 mole) of 12,12-difluoro-11-dodecen-1-ol (prepared in Example 5), 0.49 gram (0.0045 mole) of 4-methylphenol, 1.2 grams (0.0045 mole) of triphenylphosphine, and 0.79 gram (0.0045 mole) of diethyl azodicarboxylate in 25 ml of tetrahydrofuran was stirred, and the progress of the reaction was monitored by gas chromatographic analysis. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure to a residue. The residue was dissolved in 25 ml of diethyl ether, and a solid precipitate was removed by filtration. The filtrate was concentrated under reduced pressure to a residual solid. The solid was subjected to column chromatography on silica gel. Elution was accomplished using methylene chloride. The appropriate fractions were combined and concentrated under reduced pressure yielding 0.52 gram of 12,12-difluoro-11-dodecenyl 4-methylphenyl ether. The nmr spectrum was consistent with the proposed structure.

Workup

  1. customUpon completion of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure to a residue
  3. dissolutionThe residue was dissolved in 25 ml of diethyl ether
  4. customa solid precipitate was removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure to a residual solid
  6. washElution
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-20431e93db1c480392ec7fb761a11923
Source dataset
uspto-grants-1992_01
Patent number
US05081287

Reaction notes

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