Triethylamine → 3-(M-Tolyl)propyl methanesulfonate

HRID 411642Notes

Reaction equation

HRID 411642 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][OH:11])[CH:5]=[CH:6][CH:7]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14].CCN(CC)CC>C(Cl)Cl>[C:2]1([CH3:1])[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH2:10][O:11][S:13]([CH3:12])(=[O:15])=[O:14])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 102612513-(3-Methylphenyl)propan-1-ol

Product 1

HCID 539657943-(M-Tolyl)propyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3-(m-Methylphenyl)-1-propanol (0.45 g, 3.00 mmol), MsCl(278 uL, 3.60 mmol) and Et3N (0.84 mL, 6.00 mmol) were combined in CH2Cl2 (30 mL) and stirred at 0° C. for 4 hrs. The reaction was then diluted with CH2Cl2 (30 mL) and washed with cold brine, dried over Na2SO4 and concentrated to give a light brown oil. This was used without further purification. 1H NMR (300 MHz, CDCl3) δ 2.04-2.09 (m, 2H), 2.33(s, 3H), 2.69-2.74 (t, 2H), 2.99 (s, 3H), 4.20-4.24 (t, 2H), 6.97-7.04 (m, 3H), 7.16-7.19 (m, 1H).

Workup

  1. washwashed with cold brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give a light brown oil
  5. customThis was used without further purification

Sources & evidence

ORD record
ord-a60fb841029445dcb957ebd85e14e7f2
Source dataset
uspto-grants-2003_05
Patent number
US06559172B1

Reaction notes

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