Methanol → HCID 13170093, compound

HRID 365971Notes

Reaction equation

HRID 365971 reaction equation
CO.[CH3:3][O:4][C@@H:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][C@H:6]1OS(C)(=O)=O.C[O-].[Na+]>O>[CH3:3][O:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6]1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 53654929HCID 53654929, compound

Product 1

HCID 13170093HCID 13170093, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A stirrer, thermometer and reflux condenser were mounted to a 500-ml four-necked flask which was filled with 200 ml of methanol and 12.1 g (0.05 mol) of trans-1-methoxy-2-methane sulfonyloxy indane, and cooled in an ice-salt bath to 0° C. The cream-colored slurry was stirred while 27 g (0.5 mol) of sodium methoxide was added. The reaction liquid was heated to 70° C., stirred for 6 hours, cooled to 25° C., 200 ml of water was added, and extraction was performed twice with 200 ml of methylene chloride and the methylene chloride layer was dried with anhydrous sodium sulfate and vacuum-concentrated to obtain 7.17 g of a reddish-brown oil of 1-methoxyindene (yield of 98.2%). The purity of this compound according to gas chromatography (GC) was 90.9% (surface area percentage). Its physical properties are given below.

Workup

  1. temperatureA stirrer, thermometer and reflux condenser
  2. customwere mounted to a 500-ml four-necked flask
  3. additionwas added
  4. customThe reaction liquid
  5. temperaturewas heated to 70° C.
  6. temperaturecooled to 25° C.
  7. extractionextraction
  8. dry with materialthe methylene chloride layer was dried with anhydrous sodium sulfate
  9. concentrationvacuum-concentrated

Sources & evidence

ORD record
ord-61d359b4e10c48eb9889da8fe0de12d4
Source dataset
uspto-grants-2000_10
Patent number
US06127579

Reaction notes

Loading…