Cornforth reagent → HCID 22120168, compound

HRID 963535Notes

Reaction equation

HRID 963535 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH3:22][C:23]1([CH3:48])[CH2:32][CH2:31][C:30]([CH3:34])([CH3:33])[C:29]2[CH:28]=[C:27]([O:35][C:36]3[CH:37]=[C:38]4[C:43](=[CH:44][CH:45]=3)[C:42]([CH2:46][OH:47])=[CH:41][CH:40]=[CH:39]4)[CH:26]=[CH:25][C:24]1=2>ClCCl>[CH3:22][C:23]1([CH3:48])[CH2:32][CH2:31][C:30]([CH3:33])([CH3:34])[C:29]2[CH:28]=[C:27]([O:35][C:36]3[CH:37]=[C:38]4[C:43](=[CH:44][CH:45]=3)[C:42]([CH:46]=[O:47])=[CH:41][CH:40]=[CH:39]4)[CH:26]=[CH:25][C:24]1=2

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 22120170HCID 22120170, compound

Product 1

HCID 22120168HCID 22120168, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

100 ml of dichloromethane and 1.7 g (4.5 mmol) of pyridinium dichromate were introduced into a round-bottomed flask. The mixture was cooled to 0° C. and a solution of 1.2 g (3.3 mmol) of 6-(5,6,7,8-tetra-hydro-5,5,8,8-tetramethyl-2-naphthyloxy)naphthalene methanol in 20 ml of dichloromethane was added dropwise. The mixture was stirred at room temperature for one hour, the reaction medium was filtered over silica, the filtrate was evaporated to dryness and the solid was triturated in heptane and filtered off. 1.07 g (90%) of the expected aldehyde was recovered, having a melting point of 123°-4° C.

Workup

  1. filtrationthe reaction medium was filtered over silica
  2. customthe filtrate was evaporated to dryness
  3. customthe solid was triturated in heptane
  4. filtrationfiltered off
  5. custom1.07 g (90%) of the expected aldehyde was recovered

Sources & evidence

ORD record
ord-8e466351ca0c4dd7aa3df4768dd8114d
Source dataset
uspto-grants-1998_06
Patent number
US05763487

Reaction notes

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