Benzene → HCID 53971628, compound

HRID 1532928Notes

Reaction equation

HRID 1532928 reaction equation
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]1[CH:5]=[C:6]([OH:12])[C:7](=[CH:10][CH:11]=1)[CH:8]=O)[CH3:2].[C:15]([CH:18]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:17])=[O:16].[CH:38]1C=CC=C[CH:39]=1>>[CH2:38]([O:17][C:15](=[O:16])[CH:18]=[CH:8][C:7]1[CH:10]=[CH:11][C:4]([N:3]([CH2:13][CH3:14])[CH2:1][CH3:2])=[CH:5][C:6]=1[OH:12])[CH3:39]

Participants

4

Reactant 3

HCID 241BenzeneHCID 872934-(Diethylamino)-2-hydroxybenzaldehydeHCID 10870911Carboxymethylene triphenylphosphorane

Product 1

HCID 53971628HCID 53971628, compoundYield 70%

Procedure

4-Diethylaminosalicylaldehyde (25.0 g, 129 mmol; Tokyo Kasei Ind. Co. Ltd.) and carboxymethylidene-triphenylphosphorane (49.0 g, 140 mmol; Aldrich Inc.) were stirred in 300 ml of anhydrous benzene at room temperature overnight under a nitrogen atmosphere and the reaction was allowed to complete, during which period the reaction was conducted in a dark room. Then, the solvent was removed in vacuo, and the resulting crude product was crudely purified by silica gel column chromatography (hexane/ethyl acetate 1:1 as a developing solvent) to give a mixture of cis- and trans-isomers. Further, this mixture was purified by column chromatography using aminopropyl-modified silica gel (300 g of NHDM-1020 silica gel available from Fuji Silicia Chemicals Co. Ltd; n-hexane/ethyl acetate 2:1 which elutes only the cis-isomer and chloroform/methanol 4:1 which elutes only the trans-isomer) to give 23.7 g of the desired product in 70% yield.

Workup

  1. customThen, the solvent was removed in vacuo
  2. customthe resulting crude product was crudely purified by silica gel column chromatography (hexane/ethyl acetate 1:1 as a developing solvent)
  3. customto give
  4. additiona mixture of cis- and trans-isomers
  5. customFurther, this mixture was purified by column chromatography

Sources & evidence

ORD record
ord-d5a12c27fa2d4855a8b0453a3b925e5d
Source dataset
uspto-grants-2001_03
Patent number
US06207365B1

Reaction notes

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