Hydrochloric Acid → 3,5,6,7-tetrahydro-s-indacen-1(2H)-one

HRID 1276538Notes

Reaction equation

HRID 1276538 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH2:11][CH2:10][CH2:9]2)=[O:5].Cl>S(=O)(=O)(O)O>[C:4]1(=[O:5])[C:6]2[C:14](=[CH:13][C:12]3[CH2:11][CH2:10][CH2:9][C:8]=3[CH:7]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 32867585-(3-Chloropropionyl)indan

Product 1

HCID 109318913,5,6,7-tetrahydro-s-indacen-1(2H)-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Concentrated sulfuric acid (550 mL) was added dropwise, with stirring over a time period of 2 hours to 137 grams of 3-chloro-1-indan-5-yl-propan-1-one. The resulting thick black solution was heated to 90° C. until hydrogen chloride evolution ceased (usually 1-4 hours). The mixture was then cooled to room temperature and poured onto 5 kg of ice. The resulting slurry was stirred overnight and filtered. The solid was washed with water until the water ran clear through the filter. The tan solid was then dried in vacuo and recrystallized from hexane to afford 90 grams of the title compound, m.p. 72.4-74.8° C.

Workup

  1. customusually 1-4 hours
  2. filtrationfiltered
  3. washThe solid was washed with water until the water
  4. customThe tan solid was then dried in vacuo
  5. customrecrystallized from hexane

Sources & evidence

ORD record
ord-90427445a225400eab23a52895d3c9a0
Source dataset
uspto-grants-2000_12
Patent number
US06166064

Reaction notes

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