3-Phenoxybenzaldehyde → HCID 54170266, compound

HRID 1383234Notes

Reaction equation

HRID 1383234 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([O:18][C:19]([CH:21]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:20])[CH3:17]>O1CCOCC1.C(OCC)(=O)C.CCCCCCC.C(OCC)(=O)C>[O:1]([C:8]1[CH:9]=[C:10]([CH:11]=[CH:21][C:19]([O:18][CH2:16][CH3:17])=[O:20])[CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 382843-PhenoxybenzaldehydeHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

Product 1

HCID 54170266HCID 54170266, compoundYield 76.5%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

To a stirred solution of 23.4 g (0.188 mole) of 3-phenoxybenzaldehyde in 175 mL of 1,4-dioxane was added 45.2 grams (0.130 mole) of ethoxycarbonylmethylenetriphenylphosphorane in one portion. The reaction was allowed to stir at ambient temperature overnight. The solvent was evaporated under reduced pressure, leaving a residue which was dissolved in ethyl acetate. Approximately 30 grams of silica gel was mixed with this solution. This solvent was evaporated under reduced pressure, and the silica gel was placed in a sintered glass filter. The silica gel was eluted with 1000 mL of heptane/ethyl acetate (3:1). The solvent was evaporated under reduced pressure, leaving an oil. This oil was dissolved in 150 mL of heptane/ethyl acetate (9:1), treated with 15 grams of silica gel, and filtered. The filtrate was evaporated under reduced pressure, leaving 26.7 grams of ethyl 3-(3-phenoxyphenyl)acrylate as an oil. The nmr spectrum was consistent with the proposed structure.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customleaving a residue which
  3. additionApproximately 30 grams of silica gel was mixed with this solution
  4. customThis solvent was evaporated under reduced pressure
  5. filtrationfilter
  6. washThe silica gel was eluted with 1000 mL of heptane/ethyl acetate (3:1)
  7. customThe solvent was evaporated under reduced pressure
  8. customleaving an oil
  9. additiontreated with 15 grams of silica gel
  10. filtrationfiltered
  11. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d2b3a63024c34541a63ef7124881eb0f
Source dataset
uspto-grants-1989_02
Patent number
US04808762

Reaction notes

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