Resorcinol → HCID 64750293, compound

HRID 871182Notes

Reaction equation

HRID 871182 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[CH2:9]([CH:11]1[CH2:16][CH2:15][CH:14](O)[CH2:13][CH2:12]1)[CH3:10].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>[CH2:9]([CH:11]1[CH2:16][CH2:15][CH:14]([O:2][C:1]2[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][CH:8]=2)[CH2:13][CH2:12]1)[CH3:10]

Participants

6

Reactant 4

HCID 5054ResorcinolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 782934-Ethylcyclohexanol

Product 1

HCID 64750293HCID 64750293, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a four necked flask (2 L) sufficiently dried, substituted with nitrogen, and equipped with a dropping funnel, Dimroth condenser tube, thermometer and stirring blade, resorcinol (72 g, 0.65 mol), 4-ethylcyclohexanol (92 g, 0.72 mol) and triphenylphosphine (185 g, 0.70 mol) were dissolved in dried tetrahydrofuran (700 ml) under a nitrogen gas stream, and a mixed solution of diisopropyl azodicarboxylate (132 g, 0.65 mol) and dried tetrahydrofuran (180 ml) was dropped for 1 hour while cooling with an iced saline solution. Next, it was stirred at room temperature for 12 hours. After the reaction terminated, 30% hydrogen peroxide (140 ml) was dropped through the dropping funnel for 10 minutes, then the reaction solution was dissolved in 1 L toluene, and washed three times with 500 ml water. Toluene was distilled away by evaporation, and the residue was purified by column chromatography using hexane and ethyl acetate as developing solvents, to obtain a red brown objective product (hereinafter, referred to as R-3A) (38.5 g, 27% yield, 99% GC purity).

Workup

  1. customIn a four necked flask (2 L) sufficiently dried
  2. customequipped with a dropping funnel, Dimroth condenser tube
  3. temperaturewhile cooling with an iced saline solution
  4. customAfter the reaction terminated
  5. addition30% hydrogen peroxide (140 ml) was dropped through the dropping funnel for 10 minutes
  6. dissolutionthe reaction solution was dissolved in 1 L toluene
  7. washwashed three times with 500 ml water
  8. distillationToluene was distilled away by evaporation
  9. customthe residue was purified by column chromatography
  10. customto obtain a red brown objective product (hereinafter,

Sources & evidence

ORD record
ord-9bdf10737c76466da17ba3294da4ff63
Source dataset
uspto-grants-2015_03
Patent number
US08969629B2

Reaction notes

Loading…