Methanol → Methyl (2,3-dihydro-1H-inden-2-yl)acetate

HRID 2215277Notes

Reaction equation

HRID 2215277 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][C:11]([OH:13])=[O:12].S(Cl)(Cl)=O.[CH3:18]O>>[CH3:18][O:12][C:11](=[O:13])[CH2:10][CH:2]1[CH2:1][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 51749552-(2,3-dihydro-1H-inden-2-yl)acetic Acid

Product 1

HCID 14090225Methyl (2,3-dihydro-1H-inden-2-yl)acetateYield 97%

Procedure

A solution of indan-2-yl-acetic acid (Lancaster, 20 g, 0.11 mol) in methanol (200 mL) was stirred and cooled to 0–10° C. in an ice bath and treated drop-wise with thionyl chloride (14.8 g, 0.125 mol). The mixture was stirred at RT for 16 h, concentrated in vacuo, and the oily residue was dissolved in ethyl acetate, washed with 2.5 N sodium hydroxide, water, and brine, dried (MgSO4), and concentrated in vacuo to give the title compound (21 g, 97%) which solidified.

Workup

  1. temperaturecooled to 0–10° C. in an ice bath
  2. concentrationconcentrated in vacuo
  3. dissolutionthe oily residue was dissolved in ethyl acetate
  4. washwashed with 2.5 N sodium hydroxide, water, and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-21dd31f7001443c694ea2430201ad120
Source dataset
uspto-grants-2006_09
Patent number
US07109238B2

Reaction notes

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