Water → HCID 21887967, compound

HRID 1064378Notes

Reaction equation

HRID 1064378 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 methanesulfonyl chloride in 100 mL of dry CH2Cl2, keeping the temperature below 15° C. The reaction mixture was allowed to warm to room temperature 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 and washed with 1N HCl and successively with saturated NaHCO3 solution, 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 temperature in 2 h
  3. customthe organic phase was collected
  4. customthe solvent was removed in vacuo
  5. washwashed with 1N HCl and successively with saturated NaHCO3 solution
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-966f21dcc3b74ac2b3ff8d5cb686e105
Source dataset
uspto-grants-2005_11
Patent number
US06969724B2

Reaction notes

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