Ammonium Chloride → 3,3-Di-(benzylthiomethyl)hexan-2-ol

HRID 129313Notes

Reaction equation

HRID 129313 reaction equation
[CH2:1]([S:8][CH2:9][C:10]([CH2:16][S:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH2:13][CH2:14][CH3:15])[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][Mg]I.[Cl-].[NH4+]>C(OCC)C>[CH2:18]([S:17][CH2:16][C:10]([CH2:9][S:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH2:13][CH2:14][CH3:15])[CH:11]([OH:12])[CH3:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 193734152,2-Di(benzylthiomethyl)pentanalHCID 178418373HCID 178418373, compound

Product 1

HCID 193733193,3-Di-(benzylthiomethyl)hexan-2-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2,2-di-(benzylthiomethyl)pentanal (3.54 g) in dry diethyl ether was added dropwise to a stirred solution of methyl magnesium iodide [prepared from methyl iodide (1.2 ml) and magnesium (0.48 g)] in dry diethyl ether (60 ml). The reaction mixture was refluxed for 2 hours and then cooled. Saturated aqueous ammonium chloride solution was added. The mixture was stirred for 30 minutes and extracted with diethyl ether. The ethereal extracts were dried over anhydrous magnesium sulphate and the solvent was removed in vacuo. 3,3-Di-(benzylthiomethyl)hexan-2-ol was obtained as a yellow oil (1.7 g)

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. temperaturecooled
  3. extractionextracted with diethyl ether
  4. dry with materialThe ethereal extracts were dried over anhydrous magnesium sulphate
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b0ea86d5aff14b87a25e4e3b8eb6124b
Source dataset
uspto-grants-1995_11
Patent number
US05466710

Reaction notes

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