Thionyl Chloride → 6-Methoxy-2-phenylindan-1-one

HRID 31240

Reaction equation

HRID 31240 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([OH:13])=O)=[CH:5][CH:4]=1.S(Cl)(Cl)=O>C(Cl)Cl.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6]([CH2:9][CH:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:11]2=[O:13])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 977393-(4-Methoxyphenyl)-2-phenylpropionic acid

Product 1

HCID 224653766-Methoxy-2-phenylindan-1-oneYield 67.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To solution of 3-(4-methoxyphenyl)-2-phenylpropionic acid (4.6 g) in dry methylenechloride (26 ml) was added two drops of dry DMF. Thionylchloride (3 ml) was added and reaction mixture was stirred at 40° C. for 4 h. Solvent was evaporated under vacuum. Precipitate was dissolved to methylenechloride. Solution was cooled to 0-3° C. This solution and aluminium chloride (2.5g) were mixed slowly over 4 hours keeping temperature under 4° C. After mixing reaction mixture was stirred at room temperature for 2 h. Reaction was quenched by pouring to dilute ice cold hydrochloric acid. Layers were separated and water solution was extracted with methylenechloride. Combined organic layers were washed with water, dried and evaporated. Crude product was triturated to give 2.9 g of 6-Methoxy-2-phenylindan-1-one. 1H-NMR (400 MHz, d6-DMSO): 7.56 (d, 1H), 7.35-7.23 (m, 4H), 7.18-7.13 (m, 3H), 4.02 (dd, 1H, J 3.9, 8.0 Hz), 3.82 (s, 3H), 3.61 (dd, 1H, J 8.0, 17.2 Hz), 3.11 (dd, 1H, J 3.9, 17.2 Hz).

Workup

  1. customreaction mixture
  2. customSolvent was evaporated under vacuum
  3. dissolutionPrecipitate was dissolved to methylenechloride
  4. temperatureSolution was cooled to 0-3° C
  5. additionThis solution and aluminium chloride (2.5g) were mixed slowly over 4 hours
  6. customunder 4° C
  7. additionAfter mixing
  8. customreaction mixture
  9. stirringwas stirred at room temperature for 2 h
  10. customReaction
  11. customwas quenched
  12. additionby pouring to dilute ice cold hydrochloric acid
  13. customLayers were separated
  14. extractionwater solution was extracted with methylenechloride
  15. washCombined organic layers were washed with water
  16. customdried
  17. customevaporated
  18. customCrude product was triturated

Sources & evidence

ORD record
ord-af447a9e65db409095c0b2ae01d0ba0a
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Linked notes

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