Potassium Carbonate → HCID 70185365, compound

HRID 355475Notes

Reaction equation

HRID 355475 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C1(C)C=CC(S(O[CH2:26][C@H:27]2[CH2:31][O:30][C:29]([CH3:33])([CH3:32])[O:28]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:32][C:29]1([CH3:33])[O:28][C@@H:27]([CH2:26][O:1][C:2]2[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=[C:4]([CH:3]=2)[C:12]([O:14][CH3:15])=[O:13])[CH2:31][O:30]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl esterHCID 6993835(R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate

Product 1

HCID 70185365HCID 70185365, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.1 g of dimethyl 5-hydroxy-isophthalate and 2.9 g of (R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl toluene-4-sulfonate were stirred at reflux for 3 hours in 120 ml of dimethylformamide with the addition of 6.9 g of potassium carbonate. The reaction mixture was poured on to ice-water, extracted with methylene chloride, the combined methylene chloride phases were washed with water, dried over magnesium sulfate, filtered and evaporated. There was obtained dimethyl (S)-5-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-isophthalate, MS: m/z 324 ([M]+).

Workup

  1. extractionextracted with methylene chloride
  2. washthe combined methylene chloride phases were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-421dcdf83d934070a3b6fced44968ebd
Source dataset
uspto-grants-1998_11
Patent number
US05830920

Reaction notes

Loading…