2-Octanol → HCID 10943710, compound

HRID 256789Notes

Reaction equation

HRID 256789 reaction equation
[CH3:1][CH:2]([OH:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(N(C(C)C)CC)(C)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[S:20]([O:9][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:1])([CH3:19])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 200832-OctanolHCID 31297Methanesulfonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 10943710HCID 10943710, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 130 g (0.995 mol) of 2-octanol and 207 ml (1.19 mol, 1.2 equiv) of diisopropylethylamine in 1.5 L dichloromethane at 0° C. under a CaSO4 drying tube was added dropwise 84.4 ml (1.09 mol, 1.1 equiv.) of methanesulfonyl chloride over 1 hour while keeping the internal temperature at less than 5° C. The faintly yellow solution was stirred at 0° C. for an additional 1.5 h. The cold reaction solution was then washed with 2×1 L ice-cold 1M HCl and 1 L of ice-cold H2O and brine and dried over MgSO4. The residue was filtered through Celite and concentrated in vacuo below 35° C. to afford 208 g of a yellow oil. The yellow oil was placed under high-vacuum for 2 h at 25° C. to give 205 g of yellow oil. NMR spectra confirmed the desired title-product having only trace amounts of solvents present.

Workup

  1. customat less than 5° C
  2. washThe cold reaction solution was then washed with 2×1 L ice-cold 1M HCl and 1 L of ice-cold H2O and brine
  3. dry with materialdried over MgSO4
  4. filtrationThe residue was filtered through Celite
  5. concentrationconcentrated in vacuo below 35° C.

Sources & evidence

ORD record
ord-3ded2764f23748e490e9f8fc37fe95ea
Source dataset
uspto-grants-1993_11
Patent number
US05260049

Reaction notes

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