Reaction #2803

Reaction equation

mesyl chloride

lithium chloride

2-(2-hydroxymethyl-phenyl)-ethanol

collidine

→

title compound

Yield 45.0%

Methanesulfonic acid 2-(2-chloromethyl-phenyl)-ethyl ester

Yield 45.0%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   TemperatureCool in an ice bath
2. 2
   Otherpartition between ice water (300 mL)
3. 3
   workup.ADDITIONa 1:1 mixture of ether
4. 4
   WashWash the organic layer with a saturated solution of CuSO4 (2×200 mL)
5. 5
   Dryingdry (MgSO4)
6. 6
   Otherpurify by silica gel chromatography (2.5:1 hexane/ethyl acetate followed by 2:1 hexane/ethyl acetate followed by 3:2 hexane/ethyl acetate)

Procedure

Mix 2-(2-hydroxymethyl-phenyl)-ethanol (12.0 g, 78.8 mmol) and collidine (23 mL, 0.17 mol) and treat with lithium chloride (7.35 g, 0.173 mmol) in dimethylformamide (125 mL). Cool in an ice bath and treat, by dropwise addition, with mesyl chloride (13.4 mL). Stir at 0° C. for 4 hours, partition between ice water (300 mL) and a 1:1 mixture of ether:pentane (2×400 mL). Wash the organic layer with a saturated solution of CuSO4 (2×200 mL), dry (MgSO4) and purify by silica gel chromatography (2.5:1 hexane/ethyl acetate followed by 2:1 hexane/ethyl acetate followed by 3:2 hexane/ethyl acetate) to give the title compound as a pale yellow oil (8.8 g, 45%).

Source