Benzoyl chloride → 3-(2-Benzoyloxy-1,1-dimethyl-ethyl)-4-benzoyloxyphenyl methanesulphonate

HRID 971941Notes

Reaction equation

HRID 971941 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][S:11]([O:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([C:22]([CH3:26])([CH3:25])[CH2:23][OH:24])[CH:16]=1)(=[O:13])=[O:12]>C(OCC)C.[OH-].[Na+]>[CH3:10][S:11]([O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:17]([C:22]([CH3:26])([CH3:25])[CH2:23][O:24][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:16]=1)(=[O:13])=[O:12]

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 233412804-Hydroxy-3-(2-hydroxy-1,1-dimethylethyl)phenyl methanesulphonate

Product 1

HCID 233413033-(2-Benzoyloxy-1,1-dimethyl-ethyl)-4-benzoyloxyphenyl methanesulphonate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

Benzoyl chloride (5.6g) in diethyl ether (50 ml) was added dropwise with vigorous stirring to a solution of 3-(2-hydroxy-1,1-dimethylethyl)-4-hydroxyphenyl methanesulphonate in aqueous sodium hydroxide solution (1.6g in 100 ml water). The mixture was stirred for three hours at room temperature, then separated, and the ether solution washed with dilute sodium hydroxide solution followed by water. Drying over magnesium sulphate and running down gave 4.5g of an oil. Crystallization from ethanol gave 0.7g of 3-(2-benzoyloxy-1,1-dimethyl-ethyl)-4-benzoyloxyphenyl methanesulphonate, m.p. 100°-101° C. Removal of the solvent from the mother liquors gave 2.5g of 3-(2-benzoyloxy-1,1-dimethyl-ethyl)-4-hydroxyphenyl methanesulphonate as a viscous oil.

Workup

  1. customseparated
  2. washthe ether solution washed with dilute sodium hydroxide solution
  3. dry with materialDrying over magnesium sulphate
  4. customCrystallization from ethanol

Sources & evidence

ORD record
ord-1389227cd3a5429a99d3ec8879e276c6
Source dataset
uspto-grants-1979_07
Patent number
US04162154

Reaction notes

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