Potassium Carbonate → HCID 21856730, compound

HRID 1678979Notes

Reaction equation

HRID 1678979 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][C:9]=1[C:18]([O:20]C)=[O:19].[CH3:22][S:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:25]=1.[OH-].[Na+]>[N+](C1C=CC=CC=1)([O-])=O.[Cu].C(O)C.O>[CH3:22][S:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=2[C:18]([OH:20])=[O:19])=[C:26]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:25]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 2824912Dimethyl 4-bromoisophthalateHCID 20299087HCID 20299087, compound

Product 1

HCID 21856730HCID 21856730, compoundYield 74.7%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 7416NitrobenzeneSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
140 °C

Procedure

0.4 g of copper powder and 5.5 g (0.04 mole) of potassium carbonate were added to a solution of 5.5 g (0.02 mole) of dimethyl 4-bromoisophthalate and 4.5 g (0.02 mole) of 4-methylthio-2-(n-hexyl)-phenol in 40 ml of nitrobenzene and the mixture was heated under a nitrogen atmosphere at 140° C for 3 hours and then was cooled. A solution of 3.2 g (0.08 mole) of sodium hydroxide in 60 ml of a 3-1 ethanol-water mixture was added thereto and the mixture was refluxed for 1 hour and then was poured into ice water. The mixture was extracted 3 times with dichloromethane and the aqueous phase was acidified with dilute hydrochloric acid and was filtered. The recovered solid was crystallized from methanol to obtain 5.8 g of 4-[4'-methylthio-2'-(n-hexyl)-phenoxy]-isophthalic acid.

Workup

  1. temperaturewas cooled
  2. temperaturethe mixture was refluxed for 1 hour
  3. extractionThe mixture was extracted 3 times with dichloromethane
  4. filtrationwas filtered
  5. customThe recovered solid was crystallized from methanol

Sources & evidence

ORD record
ord-e2e6f7f2b5f443ada0292b998b1aeade
Source dataset
uspto-grants-1978_03
Patent number
US04078078

Reaction notes

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