Hydrochloric Acid → HCID 22246935, compound

HRID 2298142Notes

Reaction equation

HRID 2298142 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:5]=[O:6].[CH:11]([Mg]Br)=[CH2:12].Cl.CCOC(C)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[CH:11]=[CH2:12])[CH:7]=[C:8]([Cl:10])[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 357463,5-DichlorobenzaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 22246935HCID 22246935, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,5-dichlorobenzaldehyde (7.5 g, 43 mmol) in THF (75 mL) was cooled to 0° C. and vinylmagnesium bromide (1M in THF, 48 mL, 48 mmol) was added dropwise. The reaction was warmed to room temperature and was stirred overnight. Aqueous HCl (1N) and EtOAc were added. The aqueous solution was extracted with EtOAc and the organic solution was dried (MgSO4), filtered, and concentrated. The residue was used in the next step without further purification.

Workup

  1. extractionThe aqueous solution was extracted with EtOAc
  2. dry with materialthe organic solution was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was used in the next step without further purification

Sources & evidence

ORD record
ord-e43d1f7962a04a88a39d197d177f9b40
Source dataset
uspto-grants-2002_12
Patent number
US06492412B2

Reaction notes

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