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

HRID 2170922Notes

Reaction equation

HRID 2170922 reaction equation
[CH3:1][C:2]([OH:7])([CH3:6])[CH2:3][CH2:4][OH:5].N1C=CC=CC=1.[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.Cl>C(Cl)Cl>[OH:7][C:2]([CH3:6])([CH3:1])[CH2:3][CH2:4][O:5][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:14])=[CH:16][CH:17]=1)(=[O:23])=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 247470Isopentyldiol

Product 1

HCID 140012952-Methyl-4-[(4-methylbenzenesulfonyl)oxy]butan-2-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.0 ml (93.7 mmol) of 3-methylbutane-1,3-diol and 7.60 ml (94.9 mmol) pyridine are dissolved in 100 ml DCM. The mixture is cooled in an ice bath. 15.0 g (78.7 mmol) of 4-methylbenzenesulfonyl chloride are added portionwise. The reaction mixture is stirred at r.t. for 16 h. The reaction mixture is poured into 100 ml of 1N aq. HCl and stirred for 10 min. Then the layers are separated. The aq. layer is extracted with DCM. The combined organic layers are washed with brine and dried. The solvent is evaporated and the residue is chromatographed on silica gel (PE/EtOAc) to give the title compound. Yield: 15.3 g; Mass spectrum (ESI+): m/z=276 [M+NH4]+.

Workup

  1. temperatureThe mixture is cooled in an ice bath
  2. stirringstirred for 10 min
  3. customThen the layers are separated
  4. extractionThe aq. layer is extracted with DCM
  5. washThe combined organic layers are washed with brine
  6. customdried
  7. customThe solvent is evaporated
  8. customthe residue is chromatographed on silica gel (PE/EtOAc)

Sources & evidence

ORD record
ord-c5e6599310ec4ce4bd9bea560c2dcc6b
Source dataset
uspto-grants-2015_06
Patent number
US09051289B2

Reaction notes

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