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Dimethyl Sulfoxide → 4-(4-Isopropyl-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexanal

HRID 1362525
Notes
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Reaction equation

HRID 1362525 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:20][CH3:21])[CH2:11][C:12]([OH:19])([C:15]([F:18])([F:17])[F:16])[CH2:13][OH:14])=[C:6]([O:22][CH3:23])[CH:5]=1)([CH3:3])[CH3:2].C(C1C=CC(C(C)C(C)C(O)(C(F)(F)F)CO)=C(OC)C=1)(C)C.CS(C)=O.[NH4+].[Cl-]>ClCCl.C(N(CC)CC)C>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:20][CH3:21])[CH2:11][C:12]([OH:19])([C:15]([F:17])([F:16])[F:18])[CH:13]=[O:14])=[C:6]([O:22][CH3:23])[CH:5]=1)([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 25517Ammonium ChlorideHCID 669694324-(4-Isopropyl-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexan-1-olHCID 669696864-(4-Isopropyl-2-methoxyphenyl)-2-hydroxy-3-methyl-2-(trifluoromethyl)pentan-1-ol

Product 1

HCID 866153304-(4-Isopropyl-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexanal

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

The above-described mixture of 4-(4-isopropyl-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexan-1-ol and 4-(4-isopropyl-2-methoxyphenyl)-2-hydroxy-3-methyl-2-(trifluoromethyl)pentan-1-ol (5.35 g, 16 mmol) is dissolved in dichloromethane (164 ml). Following addition of dimethyl sulphoxide (54.8 ml) and triethylamine (11.1 ml) the SO3/pyridine complex (6.37 g, 40 mmol) is added in portions over the course of 40 minutes. After four-hour stirring at room temperature, the batch is poured onto a mixture of saturated NH4Cl solution and ice. The mixture is extracted twice with diethyl ether (250 ml each time) and the combined extracts are washed twice with brine (50 ml each time). Following removal of the solvent by evaporation, the residue is chromatographed on silica gel (eluent: hexane/diethyl ether). This isolates 3.05 g (57%) of a mixture of the two aldehydes, 4-(4-isopropyl-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)-hexanal and 4-(4-isopropyl-2-methoxyphenyl)-2-hydroxy-3-methyl-2-(trifluoromethyl)pentanal.

Workup

  1. additionis added in portions over the course of 40 minutes
  2. extractionThe mixture is extracted twice with diethyl ether (250 ml each time)
  3. washthe combined extracts are washed twice with brine (50 ml each time)
  4. customremoval of the solvent
  5. customby evaporation
  6. customthe residue is chromatographed on silica gel (eluent: hexane/diethyl ether)

Sources & evidence

ORD record
ord-98b50374b5aa44cc8c5bf8a50f0138cc
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07880042B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes