Dichloromethane → HCID 15285889, compound

HRID 1275611Notes

Reaction equation

HRID 1275611 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([S:14][C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=3)[CH:5]=[CH:4][C:3]1=2.ClCCl.ClC1C=CC=C(C(OO)=[O:38])C=1>O>[CH3:26][C:2]1([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([S:14]([C:15]3[CH:16]=[CH:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][CH:25]=3)=[O:38])[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 10761557HCID 10761557, compound

Product 1

HCID 15285889HCID 15285889, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.1 g (3.1 mmol) of ethyl 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylthio)benzoate and 30 ml of dichloromethane were introduced into a round-bottomed flask, and 970 mg (3.1 mmol) of meta-chloroperbenzoic acid were then added. The entire contents were stirred at room temperature for two hours, the reaction medium poured into water, extracted with dichloromethane, the organic phase decanted off, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on a silica column eluted with dichloromethane. After evaporation of the solvents, 1 g (84%) of the expected ester was recovered.

Workup

  1. customthe reaction
  2. extractionextracted with dichloromethane
  3. customthe organic phase decanted off
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by chromatography on a silica column
  7. washeluted with dichloromethane
  8. customAfter evaporation of the solvents, 1 g (84%) of the expected ester
  9. customwas recovered

Sources & evidence

ORD record
ord-42a79ca4a3c4496d94079dd31c80e610
Source dataset
uspto-grants-2000_12
Patent number
US06162815

Reaction notes

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