Cyclohexanol → HCID 21476982, compound

HRID 2293544Notes

Reaction equation

HRID 2293544 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH:13]1(O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH:13]1([O:12][C:10]2[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([OH:1])[CH:11]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 7966CyclohexanolHCID 11776TriphenylphosphineHCID 16523Methyl 2,4-DihydroxybenzoateHCID 75555Diisopropyl diazene-1,2-dicarboxylate

Product 1

HCID 21476982HCID 21476982, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 3.00 g portion of methyl 2,4-dihydroxybenzoate was dissolved in 30 ml of tetrahydrofuran, and 2 ml of cyclohexanol, 9.00 g of triphenylphosphine and 7.38 ml of diisopropyl azodicarboxylate were added, followed by stirring for 12 hours at room temperature. After completion of the reaction, the solvent was evaporated, the resulting residue was mixed with hexane-ethyl acetate, and insoluble matter was removed by filtration. Solvent of the filtrate was evaporated and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=12:1-2:1) to give 1.70 g of methyl 4-cyclohexyloxy-2-hydroxybenzoate. Nuclear magnetic resonance spectrum (DMSO-d6, TMS internal standard) δ: 1.10-2.10 (10H, m), 3.86 (3H, s), 4.40-4.48 (1H, m), 6.43-6.58 (2H, m), 7.63-7.75 (1H, m), 10.71 (1H, s)

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. additionthe resulting residue was mixed with hexane-ethyl acetate, and insoluble matter
  4. customwas removed by filtration
  5. customSolvent of the filtrate was evaporated
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=12:1-2:1)

Sources & evidence

ORD record
ord-a3739f55996f4d4ea98a0c8e213f4e58
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Reaction notes

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