Cornforth reagent → HCID 15117891, compound

HRID 2107750Notes

Reaction equation

HRID 2107750 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:19]([C:22]([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:24])[CH3:23])=[CH:18][C:15]=1[CH2:16][OH:17].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl.CCOCC>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:19]([C:22]([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:23])[CH3:24])=[CH:18][C:15]=1[CH:16]=[O:17]

Participants

5

Reactant 2

HCID 2724130Cornforth reagentHCID 15117890HCID 15117890, compound

Product 1

HCID 15117891HCID 15117891, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

The above benzyl alcohol (37 g, 0.08 mol) in dichloromethane (150 ml) was added dropwise to a suspension of pyridinium dichromate (36.25 g, 0.14 mole, Tetrahedron Letters, 399 [1979]) in dichloromethane (250 ml), with stirring. Stirring was continued overnight, and then the reaction mixture was diluted with ether and filtered through a magnesium sulfatesilica gel pad. The filtrate was washed with 1N hydrochloric acid and then it was evaporated in vacuo to give 31.2 g (87% yield) of 2-(2-[2-(2-tetrahydropyranyloxy)ethoxy]ethoxy)-5-t-octylbenzaldehyde, as an oil.

Workup

  1. stirringStirring
  2. filtrationfiltered through a magnesium sulfatesilica gel pad
  3. washThe filtrate was washed with 1N hydrochloric acid
  4. customit was evaporated in vacuo

Sources & evidence

ORD record
ord-e83875589ef14acf937c42364f4920bf
Source dataset
uspto-grants-1990_06
Patent number
US04935442

Reaction notes

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