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Hydrochloric Acid → 1-((2-Benzoylphenylthio)methyl)cyclohexanecarboxaldehyde

HRID 496168
Notes
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Reaction equation

HRID 496168 reaction equation
[SH:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].S([O:20][CH2:21][C:22]1([CH:28]=O)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)(C)(=O)=O.CCOCC(OCC)COCC.Cl>COCCOCCOC>[C:4]([C:3]1[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=1[S:1][CH2:28][C:22]1([CH:21]=[O:20])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)(=[O:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5483211,2,3-TriethoxypropaneHCID 34997132-MercaptobenzophenoneHCID 223252611-(Mesyloxymethyl)cyclohexanecarboxaldehyde

Product 1

HCID 223252081-((2-Benzoylphenylthio)methyl)cyclohexanecarboxaldehydeYield 75.9%

Reagents, catalysts & solvents 1

HCID 8150
Diglyme
Solvent

Procedure

A mixture of 69 g (0.303 mole) of 2-mercaptobenzophenone, 82 g (0.303 mole) of mesylate 55, 32 g of triethyline, and 150 ml of diglyme was stirred and held at relux for 24 h. The mixture was cooled, poured into dil. HCl and extracted with methylene chloride. The organic layer was washed with 10% NaOH, water, brine, and dried over sodium sulfate and concentrated under vacuum to remove excess diglyme. This was purified by silica gel flush column (5% EtOAc-Hexane) and gave 18.6 g (75.9%) of yellow oil. Proton NMR and mass spectra were consistent with the product.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with 10% NaOH, water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customto remove excess diglyme
  7. customThis was purified by silica gel
  8. customflush column (5% EtOAc-Hexane)

Sources & evidence

ORD record
ord-0d3ac92f940f487a82ba14c43666dd6f
Source dataset
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06943189B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes