Potassium Carbonate → HCID 12138357, compound

HRID 1271673Notes

Reaction equation

HRID 1271673 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([SH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:13]([C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:24]=1)[CH2:20]Br)([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:13]([C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:24]=1)[CH2:20][S:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([S:12][CH2:20][C:19]2[CH:18]=[C:17]([C:13]([CH3:15])([CH3:14])[CH3:16])[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:22]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 44475071-(Bromomethyl)-3,5-di-tert-butylbenzeneHCID 12138349HCID 12138349, compound

Product 1

HCID 12138357HCID 12138357, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 3,5-dimercaptobenzoate (20.0 g, 100.0 mmol), 3,5-di-tertiarybutylbenzyl bromide (molecular weight 283.25, 57.0 g, 201.2 mmol) and potassium carbonate (molecular weight 138.21, 28.0 g, 202.6 mmol) were dissolved, in 350 ml of acetone and the mixture was heated under reflux for 12 hours. The acetone and salts were removed, and the residue was purified by means of chromatography with dichloromethane as the developing solvent, giving methyl 3,5-bis(3,5di-tertiary-butylbenzylthio)benzoate as needles.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hours
  3. customThe acetone and salts were removed
  4. customthe residue was purified by means of chromatography with dichloromethane as the developing solvent

Sources & evidence

ORD record
ord-2ee642cbb1a84df8b5fc07f4f7ace5cb
Source dataset
uspto-grants-2007_04
Patent number
US07205428B2

Reaction notes

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