Water → HCID 11184174, compound

HRID 41844Notes

Reaction equation

HRID 41844 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O[CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH3:28])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.C1(C)C=CC=CC=1>[CH3:28][O:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 70051-NaphtholHCID 11430Potassium CarbonateHCID 11076628HCID 11076628, compound

Product 1

HCID 11184174HCID 11184174, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

In 110 g of dimethyl sulfoxide were dispersed 21.6 g (0.15 mol) of 1-naphthol, 27.4 g (0.1 mol) of 2-(2-methoxy-ethoxy)ethyl 4-toluenesulfonate, and 20.7 g (0.15 mol) of potassium carbonate. The dispersion was heated and stirred at 80° C. for 3 hours. After cooling, the solution was combined with 200 g of water and 200 g of toluene, from which an organic layer was separated. It was washed 2 times with 50 g of water, 5 times with 2.5 wt % sodium hydroxide aqueous solution and then 4 times with 100 g of water. The organic layer was concentrated, obtaining 21 g of oily matter. On vacuum distillation (120° C./0.06 Torr), 18.6 g of the target compound was recovered (yield 75%).

Workup

  1. temperatureThe dispersion was heated
  2. temperatureAfter cooling
  3. customwas separated
  4. washIt was washed 2 times with 50 g of water, 5 times with 2.5 wt % sodium hydroxide aqueous solution
  5. concentrationThe organic layer was concentrated
  6. customobtaining 21 g of oily matter
  7. distillationOn vacuum distillation (120° C./0.06 Torr), 18.6 g of the target compound
  8. customwas recovered (yield 75%)

Sources & evidence

ORD record
ord-394873459eb840e5ae82bc4f6c767647
Source dataset
uspto-grants-2013_09
Patent number
US08535869B2

Reaction notes

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