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

HRID 1623658Notes

Reaction equation

HRID 1623658 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 (2.5 g, 14.87 mmol), potassium carbonate (25 g, 181 mmol), and dry acetone (150 ml) was stirred at room temperature for 30 min. 4-Methylbenzenesulfonyl chloride (2.86 g, 15.00 mmol) was added portionwise and the mixture was refluxed for 7 h. (Bromomethyl)benzene (6.35 g, 37.2 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 petroleum ether:ethyl acetate=4:1 to yield the title compound as a white solid. 2.6 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 petroleum ether

Sources & evidence

ORD record
ord-beb9fae8a9324c50963818d3d76bb47c
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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