Hydrochloric Acid → HCID 11118803, compound

HRID 1857536Notes

Reaction equation

HRID 1857536 reaction equation
[CH:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[CH3:13][CH2:14][O:15][C:16](/[CH:18]=[CH:19]/[CH2:20]P(OCC)(OCC)=O)=[O:17].[H-].[Na+].Cl>CN(C)C=O>[CH:1]([O:4][C:5]1[CH:12]=[CH:11][C:8](/[CH:9]=[CH:20]/[CH:19]=[CH:18]/[C:16]([O:15][CH2:14][CH3:13])=[O:17])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2500774-IsopropoxybenzaldehydeHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomers

Product 1

HCID 11118803HCID 11118803, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-isopropoxybenzaldehyde (15.0 g), triethyl 4-phosphonocrotonate (27.3 g) and N,N-dimethylformamide (DMF) (100 ml) was added oily sodium hydride (60%, 4.38 g), and the mixture was stirred for 16 hours at room temperature. The reaction mixture was poured into ice-water, and neutralized with 2N-HCl. The mixture was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate (MgSO4). The solvent was distilled off and the residue was subjected to column chromatography. From the fractions eluted with ether-hexane, ethyl (E,E)-5-(4-isopropoxyphenyl)-2,4-pentadienoate (13.7 g, 58%) was obtained. Recrystallization from ether-hexane gave colorless prisms. Melting point 64-65° C.

Workup

  1. extractionThe mixture was subjected to extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over magnesium sulfate (MgSO4)
  4. distillationThe solvent was distilled off
  5. washFrom the fractions eluted with ether-hexane

Sources & evidence

ORD record
ord-d3cc9e4f6ec14a96932be14318c8d2eb
Source dataset
uspto-grants-2000_11
Patent number
US06147099

Reaction notes

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