Benzyl Alcohol → Benzyl mesylate

HRID 1648728Notes

Reaction equation

HRID 1648728 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)Cl.O>[CH3:16][S:17]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:19])=[O:18]

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 148757Benzyl mesylateYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

Under nitrogen methylene chloride (1.4 liter), benzyl alcohol (129.6 g, 1.2 moles) and triethylamine (182 g, 1.8 moles) were combined, stirred and cooled to -5° C. in an ice-water-acetone bath. A solution of methanesulfonyl chloride (150 g, 1.31 moles) in 100 ml of methylene chloride was added over 49 minutes, maintaining the temperature between -5° and 2° C. After stirring for 10 minutes at 0°-2° C., the reaction was diluted with 500 ml of water, precooled to 5° C. The organic layer was separated, washed 2×500 ml of cold water, dried over MgSO4, filtered and evaporated in vacuo to yield title product as a light yellow oil [190 g; 85%; 1H-NMR (CDCl3) delta (ppm): 2.9 (s, 3H), 5.2 (s, 2H), 7.4 (m, 5H); Rf 0.75 (CH2Cl2 )]. This product was refrigerated until used in the next step.

Workup

  1. temperaturemaintaining the temperature between -5° and 2° C
  2. stirringAfter stirring for 10 minutes at 0°-2° C.
  3. customprecooled to 5° C
  4. customThe organic layer was separated
  5. washwashed 2×500 ml of cold water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-c8e623735e574158a77087839a069b48
Source dataset
uspto-grants-1983_11
Patent number
US04412958

Reaction notes

Loading…