Potassium Carbonate → HCID 20365487, compound

HRID 1678981Notes

Reaction equation

HRID 1678981 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][S:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:10]=1.Br[C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][C:24]=1[C:33]([O:35]C)=[O:34].[OH-].[Na+]>[N+](C1C=CC=CC=1)([O-])=O.C(O)C.O.[Cu].O>[CH3:7][S:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:23]2[CH:32]=[CH:31][C:26]([C:27]([OH:29])=[O:28])=[CH:25][C:24]=2[C:33]([OH:35])=[O:34])=[C:11]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:10]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 2824912Dimethyl 4-bromoisophthalateHCID 20365493HCID 20365493, compound

Product 1

HCID 20365487HCID 20365487, compoundYield 84.8%

Reagents, catalysts & solvents 4

HCID 23978CopperCatalystHCID 962WaterSolventHCID 7416NitrobenzeneSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
120 °C

Procedure

4.40 g (0.032 mole) of anhydrous potassium carbonate and then 0.16 g of powdered copper were added to a solution of 3.60 g (0.016 mole) of 4-methylthio-2-(n-pentyloxy)-phenol and 4.37 g (0.016 mole) of dimethyl 4-bromo-isophthalate in 40 ml of nitrobenzene and the mixture was heated with stirring at 120° C under nitrogen for 3 hours. After cooling the mixture to 100° C, a solution of 1.92 g of sodium hydroxide pellets in 50 ml of a 1--1 ethanol-water mixture was added thereto and the mixture was refluxed for one hour. The mixture was cooled and 100 ml of water were added. The mixture was extracted with 100 ml of ether and the aqueous layer was washed twice with 50 ml of ether and was then acidified with 10% hydrochloric acid. The mixture was extracted with ether and the ether extract was washed with water, dried over magnesium sulfate and evaporated to dryness under reduced pressure to obtain an off-white solid residue. The residue was triturated with petroleum ether to obtain 5.3 g of 4-[4'-methylthio-2'-(n-pentyloxy)-phenoxy]-isophthalic acid. The IR spectrum showed a bonded hydroxy at 3500 to 2200cm-1 and carboxyl at 1700cm-1.

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling the mixture to 100° C
  3. temperaturethe mixture was refluxed for one hour
  4. temperatureThe mixture was cooled
  5. extractionThe mixture was extracted with 100 ml of ether
  6. washthe aqueous layer was washed twice with 50 ml of ether
  7. extractionThe mixture was extracted with ether
  8. extractionthe ether extract
  9. washwas washed with water
  10. dry with materialdried over magnesium sulfate
  11. customevaporated to dryness under reduced pressure
  12. customto obtain an off-white solid residue
  13. customThe residue was triturated with petroleum ether

Sources & evidence

ORD record
ord-6cb30e50d4bf4568b12cce68f0b246d3
Source dataset
uspto-grants-1978_03
Patent number
US04078078

Reaction notes

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