4-Toluenesulfonyl chloride → Methyl 5-{[(4-methylphenyl)sulfonyl]oxy}-2-[(phenylmethyl)oxy]benzoate

HRID 1623659Notes

Reaction equation

HRID 1623659 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.Br[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CC(C)=O>[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O:12][C:9]2[CH:10]=[CH:11][C:2]([O:1][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[C:3]([CH:8]=2)[C:4]([O:6][CH3:7])=[O:5])(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 75077Methyl Gentisate

Product 1

HCID 86762539Methyl 5-{[(4-methylphenyl)sulfonyl]oxy}-2-[(phenylmethyl)oxy]benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl 2,5-dihydroxybenzoate (10 g, 59.5 mmol), potassium carbonate (50.0 g, 362 mmol), and dry acetone (450 ml) was stirred at room temperature for 30 min. 4-Methylbenzenesulfonyl chloride (11.44 g, 60.0 mmol) was added portionwise and the mixture was refluxed for 7 h. (Bromomethyl)benzene (25.4 g, 149 mmol) was added and the resulting mixture was refluxed overnight. After cooling, the precipitate was filtered, and the filtrate was evaporated. The residue was loaded onto a silica gel column and was eluted with hexane/ethyl acetate=4:1 to yield the title compound as a yellow solid. 22 g.

Workup

  1. additionwas added
  2. temperaturethe resulting mixture was refluxed overnight
  3. temperatureAfter cooling
  4. filtrationthe precipitate was filtered
  5. customthe filtrate was evaporated
  6. washwas eluted with hexane/ethyl acetate=4:1

Sources & evidence

ORD record
ord-e29b8f30fcd14c0b88d8cd158ad38912
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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