1,3-Propanediol → 2-(3-Ethyl-4-nitrophenyl)-2-phenyl-1,3-dioxane

HRID 2095232Notes

Reaction equation

HRID 2095232 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7])[CH3:2].[CH2:20](O)[CH2:21][CH2:22][OH:23]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([C:3]1[CH:4]=[C:5]([C:6]2([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[O:23][CH2:22][CH2:21][CH2:20][O:7]2)[CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[CH3:2]

Participants

5

Reactant 2

HCID 104421,3-PropanediolHCID 53375581(3-Ethyl-4-nitrophenyl)phenylmethanone

Product 1

HCID 593862972-(3-Ethyl-4-nitrophenyl)-2-phenyl-1,3-dioxaneYield 91.8%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A suspension of 3-ethyl-4-nitro-benzophenone (11f) (20.0 g, 78.4 mmol), 1,3-propandiol (7.15 g, 94.0 mmol), p-toluenesulfonic acid monohydrate (50 mg) in toluene (300 mL) was refluxed using a Dean-Stark-trap for 24 hours. The Dean-Stark-trap was then replaced by a Soxhlet-extractor filled with molecular sieve and the mixture was refluxed for an additional 48 hours to achieve complete conversion. The reaction mixture was then cooled to ambient temperature, washed with an aqueous, saturated solution of NaHCO3 and concentrated in vacuo until crystallization started. The suspension was cooled for 0.5 hours in an ice bath and after which the crystalline product was filtered, washed with a small volume of hexane and air dried to give 22.48 g (72 mmol, 91.5%) compound 17 as yellow crystals.

Workup

  1. temperaturewas refluxed
  2. customfor 24 hours
  3. additionfilled with molecular sieve
  4. temperaturethe mixture was refluxed for an additional 48 hours
  5. washwashed with an aqueous, saturated solution of NaHCO3
  6. concentrationconcentrated in vacuo until crystallization
  7. temperatureThe suspension was cooled for 0.5 hours in an ice bath
  8. filtrationafter which the crystalline product was filtered
  9. washwashed with a small volume of hexane and air
  10. customdried

Sources & evidence

ORD record
ord-29d66b647aaa4fc3aec59f84b1de373e
Source dataset
uspto-grants-2013_05
Patent number
US08445734B2

Reaction notes

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