Cyclohexanol → HCID 21997446, compound

HRID 1977308Notes

Reaction equation

HRID 1977308 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH:18]1(O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH:18]1([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=3)=[CH:6][CH:7]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 7966CyclohexanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1490289Methyl 4'-hydroxy(1,1'-biphenyl)-4-carboxylate

Product 1

HCID 21997446HCID 21997446, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(4-hydroxyphenyl)benzoate (3.00 g) and cyclohexanol (1.58 g) in tetrahydrofuran (60 ml) was added dropwise diethyl azodicarboxylate (2.48 ml) at 0-10° C. under nitrogen atmosphere, and the mixture was stirred at ambient temperature for 4 hours. After concentration, to the residue was added ethyl acetate (50 ml) and n-hexane (10 ml), and the resulting precipitate was removed by filtration and discarded. To the filtrate was added silica gel (12 g) and the mixture was evaporated. The residue was purified by column chromatography on silica gel (80 g) eluting with a mixed solvent of 5% ethyl acetate in n-hexane to give methyl 4-(4-cyclohexyloxyphenyl)benzoate (1.79 g) as a white solid.

Workup

  1. concentrationAfter concentration
  2. additionto the residue was added ethyl acetate (50 ml) and n-hexane (10 ml)
  3. customthe resulting precipitate was removed by filtration
  4. additionTo the filtrate was added silica gel (12 g)
  5. customthe mixture was evaporated
  6. customThe residue was purified by column chromatography on silica gel (80 g)
  7. washeluting with a mixed solvent of 5% ethyl acetate in n-hexane

Sources & evidence

ORD record
ord-26f294e77f2a40638f7e27afc20b5684
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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