Water → HCID 21887967, compound

HRID 1241873Notes

Reaction equation

HRID 1241873 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][OH:6].C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20].O>C(Cl)Cl>[CH3:18][S:19]([O:6][CH2:5][CH2:4][C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[CH3:1])(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 882672-Methylphenethyl alcohol

Product 1

HCID 21887967HCID 21887967, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

10 g (0.0734 mol) of 2-methylphenethyl alcohol were dissolved in 200 mL of dry CH2Cl2 under a nitrogen atmosphere; the solution was cooled to 5° C., 16.4 mL (0.1175 mol) of triethylamine were added, followed by a solution of 9.1 mL (0.1175 mol) of methanesulphonyl chloride in 100 mL of dry CH2Cl2, keeping the temperature below 15° C. The reaction mixture was allowed to warm to room temperate in 2 h, then 250 mL of water were added, the organic phase was collected and the solvent was removed in vacuo. The resulting oil was taken up in Et2O, the organic phase was washed with 1N HCl and with saturated NaHCO3 solution, then it was dried and the solvent was removed in vacuo, yielding 14.5 g of the title product which was used without further purification.

Workup

  1. customthe temperature below 15° C
  2. temperatureto warm to room temperate in 2 h
  3. customthe organic phase was collected
  4. customthe solvent was removed in vacuo
  5. washthe organic phase was washed with 1N HCl and with saturated NaHCO3 solution
  6. customit was dried
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-82fba3b074ba4a96877d31daa7f6a25a
Source dataset
uspto-grants-2006_10
Patent number
US07115633B2

Reaction notes

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