Hydrochloric Acid → 2-((2-Benzoylphenylthio)methyl)-2-ethylhexanal

HRID 1604491Notes

Reaction equation

HRID 1604491 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].[CH2:16]([C:18]([CH2:25]OS(C)(=O)=O)([CH2:21][CH2:22][CH2:23][CH3:24])[CH:19]=[O:20])[CH3:17].C(N(CC)CC)C.Cl>COCCOCCOC>[C:4]([C:3]1[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=1[S:1][CH2:25][C:18]([CH2:16][CH3:17])([CH2:21][CH2:22][CH2:23][CH3:24])[CH:19]=[O:20])(=[O:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 34997132-MercaptobenzophenoneHCID 115722172-Ethyl-2-(mesyloxymethyl)hexanal

Product 1

HCID 116028262-((2-Benzoylphenylthio)methyl)-2-ethylhexanalYield 58%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A mixture of 31 g (0.144 mol) of 2-mercaptobenzophenone, prepared according to the procedure described in WO 93/16055, 24.4 g (0.1 mole) of 2-ethyl-2-(mesyloxymethyl)-hexanal (1), 14.8 g (0.146 mole) of triethylamine, and 80 mL of 2-methoxyethyl ether was held at reflux for 24 h. The reaction mixture was poured into 3N HCl and extracted with 300 mL of methylene chloride. The methylene chloride layer was washed with 300 mL of 10% NaOH, dried over MgSO4 and concentrated in vacuo to remove 2-methoxyethyl ether. The residue was purified by HPLC (10% EtOAc-hexane) to give 20.5 g (58%) of 2 as an oil.

Workup

  1. customprepared
  2. temperatureat reflux for 24 h
  3. extractionextracted with 300 mL of methylene chloride
  4. washThe methylene chloride layer was washed with 300 mL of 10% NaOH
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto remove 2-methoxyethyl ether
  8. customThe residue was purified by HPLC (10% EtOAc-hexane)

Sources & evidence

ORD record
ord-2a7ed8aa3867460081d64fd8404c2622
Source dataset
uspto-grants-1999_11
Patent number
US05994391

Reaction notes

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