Hydrochloric Acid → HCID 66840740, compound

HRID 1911161Notes

Reaction equation

HRID 1911161 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[OH-].[K+].[CH3:12][CH2:13][C:14](=[O:17])[CH2:15][CH3:16].Cl>O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:13]([CH3:12])[C:14](=[O:17])[CH2:15][CH3:16])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7288Ethyl ketoneHCID 77264-ChlorobenzaldehydeHCID 14797Potassium Hydroxide

Product 1

HCID 66840740HCID 66840740, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To 4-chlorobenzaldehyde 46a (99.6 mmol, 14 g) in water (44 mL) was added KOH (44.6 mmol, 2.5 g). The mixture was heated at 65° C. and 3-pentanone (99.6 mmol, 8.58 g) was added dropwise over 10 min. After refluxing for 8 h, the reaction mixture was cooled to room temperature and stirred overnight. Following addition of 260 mL 1N aqueous HCl, the mixture was extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography (silica gel, 5% EtOAc/heptane) to give 8.59 g of 46b.

Workup

  1. temperatureAfter refluxing for 8 h
  2. temperaturethe reaction mixture was cooled to room temperature
  3. extractionthe mixture was extracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by flash column chromatography (silica gel, 5% EtOAc/heptane)

Sources & evidence

ORD record
ord-8f8bc483d59b43a6993ca85888117819
Source dataset
uspto-grants-2013_12
Patent number
US08604017B2

Reaction notes

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