Hydrochloric Acid → Tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonate

HRID 1924863Notes

Reaction equation

HRID 1924863 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.Cl>N1C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH:4]([O:7][S:14]([C:11]2[CH:12]=[CH:13][C:8]([CH3:18])=[CH:9][CH:10]=2)(=[O:16])=[O:15])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 74956Tetrahydro-4H-pyran-4-ol

Product 1

HCID 13961807Tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonateYield 93.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of tetrahydo-4-pyranol (5.00 g; 48.9 mmol) in pyridine (30 mL) at 0-5° C. was added portionwise p-toluenesulfonyl chloride (13.9 g; 73.4 mmol). The mixture slowly warmed to room temperature, stirred overnight and poured onto 30 mL conc. HCl in ice. After stirring 15 minutes the solid was filtered and dried in vacuo. Trituration with t-butyl methyl ether provided 11.7 g of the desired product. 1H NMR (CDCl3) δ 7.82 (d, 2H), 7.35 (d, 2H), 4.70 (m, 1H), 3.88 (m, 2H), 3.47 (m, 2H), 2.46 (s, 3H), 1.86 (m, 2H), 1.76 (m, 2H).

Workup

  1. stirringAfter stirring 15 minutes the solid
  2. filtrationwas filtered
  3. customdried in vacuo

Sources & evidence

ORD record
ord-e5c0d4e0b97a47e681fea44941d2d028
Source dataset
uspto-grants-2012_05
Patent number
US08178568B2

Reaction notes

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