HCID 11097812, compound → HCID 10923769, compound

HRID 256753Notes

Reaction equation

HRID 256753 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]([CH2:14][OH:15])[C:12]([CH3:17])([CH3:16])[CH2:11][C:10]([CH3:19])([CH3:18])[CH:9]=2)=[CH:4][C:3]=1[CH3:20]>CS(C)=O.C(N(CC)CC)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]([CH:14]=[O:15])[C:12]([CH3:16])([CH3:17])[CH2:11][C:10]([CH3:18])([CH3:19])[CH:9]=2)=[CH:4][C:3]=1[CH3:20]

Participants

4

Reactant 1

HCID 11097812HCID 11097812, compound

Product 1

HCID 10923769HCID 10923769, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8471TriethylamineSolvent

Procedure

Into a slurry of 61.4 g (0.222 mol) of 1-(4-fluoro-3-methylphenyl)-6-hydroxymethyl-3,3,5,5-tetramethylcyclohexene in 330 ml of DMSO and 194 ml of triethylamine is poured a solution of 106.0 g (0.666 mol) of sulfur trioxide pyridine complex in 330 ml of DMSO. The reaction mixture is then stirred for 30 min. Ice (660 g) is added and the reaction mixture is extracted twice with 300 ml of hexanes. The extracts are then backwashed thrice with 280 ml of 10% HCl, dried over anhydrous Na2SO4, filtered and concentrated in vacuo at 40° C. to yield 57.1 g (94%) of 2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethylcyclohex-2-enecarboxaldehyde suitable for use in the next step. A pure sample of 2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethylcyclohex-2-enecarboxaldehyde can be obtained via column chromatography on silica gel.

Workup

  1. extractionthe reaction mixture is extracted twice with 300 ml of hexanes
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo at 40° C.

Sources & evidence

ORD record
ord-f083bd80b6e741fe8eb265eae07c8916
Source dataset
uspto-grants-1993_11
Patent number
US05258544

Reaction notes

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