Water → HCID 13127031, compound

HRID 871180Notes

Reaction equation

HRID 871180 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)O.[C:9](=[O:12])([O-])[O-].[K+].[K+].O.Br[CH:17]1[CH2:22][CH2:21]C[CH2:19][CH2:18]1>CS(C)=O.CN(C=O)C>[CH:9]1([O:12][C:3]2[CH:1]=[CH:8][CH:7]=[CH:6][C:4]=2[OH:5])[CH2:21][CH2:22][CH2:17][CH2:18][CH2:19]1

Participants

7

Reactant 4

HCID 962WaterHCID 5054ResorcinolHCID 7960Cyclohexyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 13127031HCID 13127031, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Under a nitrogen gas stream, resorcinol (55 g, 0.5 mol), potassium carbonate (207 g, 1.5 mol), water (25 ml, 1.4 mol) and N,N-dimethylformaldehyde (500 ml) were charged to a four necked flask (2 L) sufficiently dried, substituted with nitrogen, and equipped with a dropping funnel, Dimroth condenser tube, thermometer and stirring blade, so as to prepare a dimethylformaldehyde solution. Next, bromocylcohexane (408 g, 2.5 mol) was dropped through the dropping funnel for 10 minutes at room temperature, then this solution was heated at 80° C. for 14 hours by a mantle heater while stirring, and then heated at 100° C. for 11 hours. After the reaction terminated, it was stood to cool, and after it reached room temperature, it was cooled in an ice bath. The reaction solution was dissolved in 1 L toluene, and washed three times with 500 ml water. Toluen 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-1A) (21.9 g, 23% yield, 100% GC purity). The chemical shift value (δ ppm, TMS standard) of 1H-NMR of this compound in a heavy dimethyl sulfoxide solvent was 1.1 to 2.0 (m, 10H), 4.2 (m, H), 6.3 (m, 3H), 7.0 (m, H), 9.3 (s, H).

Workup

  1. customsufficiently dried
  2. customequipped with a dropping funnel, Dimroth condenser tube
  3. customso as to prepare a dimethylformaldehyde solution
  4. stirringwhile stirring
  5. temperatureheated at 100° C. for 11 hours
  6. customAfter the reaction terminated
  7. temperatureto cool
  8. customreached room temperature
  9. temperatureit was cooled in an ice bath
  10. dissolutionThe reaction solution was dissolved in 1 L toluene
  11. washwashed three times with 500 ml water
  12. distillationToluen was distilled away by evaporation
  13. customthe residue was purified by column chromatography
  14. customto obtain a red brown objective product (hereinafter,

Sources & evidence

ORD record
ord-3ae1ffe11ec14060b08f9c473ebc74d2
Source dataset
uspto-grants-2015_03
Patent number
US08969629B2

Reaction notes

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