p-Toluenesulfonic acid → 1-[5-(3,4-Bis-hydroxymethyl-phenoxymethyl)-2-thienyl]-1-propanone

HRID 49331Notes

Reaction equation

HRID 49331 reaction equation
[CH2:1]([C:3]1([C:8]2[S:12][C:11]([CH2:13][O:14][C:15]3[CH:16]=[CH:17][C:18]([CH2:23][OH:24])=[C:19]([CH2:21][OH:22])[CH:20]=3)=[CH:10][CH:9]=2)OCC[O:4]1)[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>O.CC(C)=O>[OH:22][CH2:21][C:19]1[CH:20]=[C:15]([CH:16]=[CH:17][C:18]=1[CH2:23][OH:24])[O:14][CH2:13][C:11]1[S:12][C:8]([C:3](=[O:4])[CH2:1][CH3:2])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 20636305HCID 20636305, compound

Product 1

HCID 698251291-[5-(3,4-Bis-hydroxymethyl-phenoxymethyl)-2-thienyl]-1-propanone

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

8 g (22.8 mmol) of {5-[5-(2-ethyl-[1,3]dioxolan-2-yl)-2-thienylmethoxy]-2-hydroxymethylphenyl}methanol are dissolved in 75 mL of water and 75 mL of acetone. 1 g of para-toluenesulphonic acid is then added and the reaction medium is refluxed for 1 hour. The reaction medium is treated with sodium bicarbonate solution and extracted with ethyl acetate. The organic phases are combined, washed with water, dried and concentrated under reduced pressure. A white powder (m.p.=123° C.) is obtained (m=6.9 g; Y=100%).

Workup

  1. temperaturethe reaction medium is refluxed for 1 hour
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-83046f2c8ab84f2496e34ee51f7f544c
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

Loading…