2,4-Dichlorobenzaldehyde → HCID 72473177, compound

HRID 597871Notes

Reaction equation

HRID 597871 reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6](/[CH:8]=[CH:9]/[CH2:10]P(OCC)(OCC)=O)=[O:7].[Cl:19][C:20]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:21]=1[CH:22]=O>C1COCC1>[CH2:4]([O:5][C:6](=[O:7])[CH:8]=[CH:9][CH:10]=[CH:22][C:21]1[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:20]=1[Cl:19])[CH3:3]

Participants

5

Reactant 3

HCID 134042,4-DichlorobenzaldehydeHCID 24758Sodium hydrideHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomers

Product 1

HCID 72473177HCID 72473177, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 60% NaH in mineral oil (16 g) in 1 L THF was added triethyl 4-phosphonocrotonate (100 g). The resulting solution was stirred for 2 hr, and then a solution of 2,4-dichlorobenzaldehyde (54 g) in 200 mL THF was added thereto. The mixture was stirred at room temperature for 1 hr. The reaction was quenched by the addition of 1 L of aq. NH4Cl and the THF was evaporated. The mixture was extracted with 4×200 ml ethyl acetate and the combined organic layer washed with water, brine and dried over MgSO4 then evaporated to provide the crude product. This was purified by silica gel chromatography using 5% ethyl acetate-hexanes to give 25.9 g of 5-(2,4-dichloro-phenyl)-penta-2,4-dienoic acid ethyl ester. MS: m/e 271.04 (MH+)

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hr
  2. customThe reaction was quenched by the addition of 1 L of aq. NH4Cl
  3. customthe THF was evaporated
  4. extractionThe mixture was extracted with 4×200 ml ethyl acetate
  5. washthe combined organic layer washed with water, brine
  6. dry with materialdried over MgSO4
  7. customthen evaporated
  8. customto provide the crude product
  9. customThis was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9dc5877ea919421bb37e633daceff949
Source dataset
uspto-grants-2011_03
Patent number
US07897601B2

Reaction notes

Loading…