Hydrochloric Acid → [4-(4'-Chloro-4-methylbiphenyl-3-yl)-3,5-dioxocyclohexyl]-acetaldehyde

HRID 1027371Notes

Reaction equation

HRID 1027371 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH:15]3[C:20](=[O:21])[CH2:19][CH:18]([CH2:22][CH:23]4OCC[O:24]4)[CH2:17][C:16]3=[O:28])[CH:9]=2)=[CH:4][CH:3]=1.Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH:15]3[C:16](=[O:28])[CH2:17][CH:18]([CH2:22][CH:23]=[O:24])[CH2:19][C:20]3=[O:21])[CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 66724712HCID 66724712, compound

Product 1

HCID 86661713[4-(4'-Chloro-4-methylbiphenyl-3-yl)-3,5-dioxocyclohexyl]-acetaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4′-chloro-4-methylbiphenyl-3-yl)-5-[1,3]dioxolan-2-ylmethylcyclohexane-1,3-dione (0.275 g, 0.69 mmol) in tetrahydrofuran (5 ml) is added 6M hydrochloric acid (2 ml), and the reaction mixture is stirred at room temperature for 1.5 hours. Additional 6M hydrochloric acid (1 ml) is added and the solution is heated at 50° C. for an additional 2 hours. After cooling to room temperature the reaction mixture is concentrated and the residue partitioned between distilled water (20 ml) and dichloromethane (20 ml). After extraction of the aqueous phase with dichloromethane (3×10 ml) all organic fractions are combined then passed through a phase separator. The fitrate is concentrated in vacuo to afford [4-(4′-Chloro-4-methylbiphenyl-3-yl)-3,5-dioxocyclohexyl]-acetaldehyde as a white foam.

Workup

  1. temperaturethe solution is heated at 50° C. for an additional 2 hours
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. concentrationis concentrated
  4. customthe residue partitioned
  5. distillationbetween distilled water (20 ml) and dichloromethane (20 ml)
  6. extractionAfter extraction of the aqueous phase with dichloromethane (3×10 ml) all organic fractions
  7. concentrationThe fitrate is concentrated in vacuo

Sources & evidence

ORD record
ord-c71c27ee58be46dc85110a42a7df0572
Source dataset
uspto-grants-2014_05
Patent number
US08735322B2

Reaction notes

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