1-Pentanol → Pentyl toluene-4-sulphonate

HRID 536745Notes

Reaction equation

HRID 536745 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][CH3:5].[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1>C(Cl)Cl.N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:17][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

6

Reactant 2

HCID 62761-PentanolHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 78195Pentyl toluene-4-sulphonateYield 63.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of pentan-1-ol (9.2 mL, 85 mmol) in CH2Cl2 (70 mL) and pyridine (50 mL) was added 4-(dimethylamino)pyridine (0.52 g, 4.3 mmol) followed by p-toluenesulfonyl chloride (16.2 g, 85 mmol). The mixture was allowed to stir at ambient temperature for 18 h then was quenched with 5% aqueous HCl (10 mL) and the layers were separated. The aqueous phase was extracted with CH2Cl2 (3×5 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by column chromatography (SiO2, 75% hexanes in EtOAc) afforded the title compound (13.1 g, 53.9 mmol, 63% yield). MS (DCI/NH3) m/z 260 (M+NH4)+.

Workup

  1. customthen was quenched with 5% aqueous HCl (10 mL)
  2. customthe layers were separated
  3. extractionThe aqueous phase was extracted with CH2Cl2 (3×5 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography (SiO2, 75% hexanes in EtOAc)

Sources & evidence

ORD record
ord-a81a90d324b24a8a8778804e8bc43f0c
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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