Sulfuric Acid → HCID 20095049, compound

HRID 1770148Notes

Reaction equation

HRID 1770148 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH2:9]([CH:17]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18]1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].S(=O)(=O)(O)O>ClCCl>[CH2:9]([CH:17]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:5](=[O:7])[CH3:6])[CH:23]=2)[CH2:18]1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 20095027HCID 20095027, compound

Product 1

HCID 20095049HCID 20095049, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Subsequently, 450 ml of dry dichloromethane and 68.7 g (5.15×10-1M) of anhydrous aluminum chloride were placed in a 1 liter-reaction vessel and cooled below 0° C. To the mixture, 37.2 g (4.74×10-1M) of acetyl chloride was added dropwise in 10 minutes below 0° C. and then 90 g (3.91×10-1M) of the above prepared 2-octylindan was added dropwise below 0° C., followed by stirring for 2 hours below 0° C. and further stirring for 2 hours at room temperature. After the reaction, the reaction mixture was poured into 1 liter of ice water and 90 ml of concentrated sulfuric acid was added. The dichloromethane layer was separated from the above mixture and washed with water, followed by drying with anhydrous magnesium sulfate and distilling-off of the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=20/1) to obtain 57.6 g of 2-octyl-5-acetylindan.

Workup

  1. temperaturecooled below 0° C
  2. additionwas added dropwise below 0° C.
  3. stirringfurther stirring for 2 hours at room temperature
  4. customAfter the reaction
  5. additionwas added
  6. customThe dichloromethane layer was separated from the above mixture
  7. washwashed with water
  8. dry with materialby drying with anhydrous magnesium sulfate and distilling-off of the solvent
  9. customto obtain a crude product
  10. customThe crude product was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-d08fe370305149d5b76900ed33bcdfc1
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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