Water → 2-Methyl-4-[(4-methylbenzenesulfonyl)oxy]butan-2-ol

HRID 579392Notes

Reaction equation

HRID 579392 reaction equation
[CH3:1][C:2]([OH:7])([CH3:6])[CH2:3][CH2:4][OH:5].[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.O>N1C=CC=CC=1.C1(C)C=CC=CC=1.C(#N)C>[C:9]1([CH3:8])[CH:14]=[CH:13][C:12]([S:15]([O:5][CH2:4][CH2:3][C:2]([OH:7])([CH3:6])[CH3:1])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

7

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 247470Isopentyldiol

Product 1

HCID 140012952-Methyl-4-[(4-methylbenzenesulfonyl)oxy]butan-2-olYield 79%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 1140TolueneSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Under a nitrogen atmosphere, 3-methylbutane-1,3-diol (300 g) was dissolved in pyridine (900 ml), and a solution of 4-methylbenzenesulfonyl chloride (500 g) in toluene (900 ml) and acetonitrile (125 ml) was added dropwise over 2 hr. The reaction mixture was stirred at room temperature for 4 hr, and toluene (500 ml) and water (1800 ml) were added to allow for layer separation. The obtained organic layer was washed successively with aqueous sulfuric acid and water (twice). The solvent in the obtained organic layer was evaporated, and the residue was azeotropically evaporated with toluene (500 ml) to give the title compound (535 g).

Workup

  1. customto allow for layer separation
  2. washThe obtained organic layer was washed successively with aqueous sulfuric acid and water (twice)
  3. customThe solvent in the obtained organic layer was evaporated
  4. customthe residue was azeotropically evaporated with toluene (500 ml)

Sources & evidence

ORD record
ord-13fba2873f654242aa082e8919a1f6f3
Source dataset
uspto-grants-2015_05
Patent number
US09040717B2

Reaction notes

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