Hydrochloric Acid → HCID 9879787, compound

HRID 2119993Notes

Reaction equation

HRID 2119993 reaction equation
[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl.[CH2:14]1[C:23](=[O:24])[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15]1.O>C(O)(=O)C.C(OC(=O)C)C.CCCCCC.ClCCl>[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8](/[CH:9]=[C:22]2/[C:23](=[O:24])[CH2:14][CH2:15][C:16]3[C:21]/2=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 682662-TetraloneHCID 2203764-(Methylsulfonyl)benzaldehyde

Product 1

HCID 9879787HCID 9879787, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
7.5 °C

Procedure

4-methylsulfonylbenzaldehyde (1.0 g, 5.43 mmol) was dissolved in glacial acetic acid (20 ml) and con. Hydrochloric acid (10 ml) was added and cooled at 5-10° C. Then, beta-tetralone (0.72 ml, 5.45 mmol) was dropped slowly and stirred for 3 hours at the same temperature. At room temperature, water (200 ml) and dichloromethane (200 ml) were poured, separated with layers, washed with the saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by performing a silica gel column chromatography (an eluting agent: ethylacetate/n-hexane=2/3, v/v) and 1.32 g of the present compound (productive yield 78%) was obtained as a yellow crystal.

Workup

  1. customseparated with layers
  2. washwashed with the saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified

Sources & evidence

ORD record
ord-b023165d59f74fdfb66c23f210bc3b16
Source dataset
uspto-grants-2004_02
Patent number
US06686493B2

Reaction notes

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