Hydrochloric Acid → 4-(2-Methyl-1,3-dioxolan-2-yl)benzaldehyde

HRID 497207

Reaction equation

HRID 497207 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:13])[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][CH:3]=1.[Li]CCCC.[CH:19](N1CCCCC1)=[O:20].Cl>C1COCC1>[CH:19]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:13])[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][CH:3]=1)=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 174291-PiperidinecarboxaldehydeHCID 6149202-(4-Bromophenyl)-2-methyl-1,3-dioxolaneHCID 178418339Butyllithium

Product 1

HCID 119615844-(2-Methyl-1,3-dioxolan-2-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-(4-bromophenyl)-2-methyl-1,3-dioxolane (2.0 g, 8.23 mmol) in THF (7 ml) was added n-BuLi (1.61 M solution in hexane, 5.47 ml, 8.8 mmol) at −78° C. under nitrogen, and the mixture was stirred for 2 hour, then allowed to warm up to 0° C. for 30 min. A solution of 1-formylpiperidine (930 mg, 8.23 mmol) in THF (5 ml) was added, and the mixture was stirred for 2 hours. The mixture was made neutral by addition of 1N HCl solution, and the whole was extracted with diethylether. The organic layer was washed with saturated NaHCO3 aqueous solution, brine, dried over MgSO4, and concentrated in vacuo. The compound was used for next reaction without purification.

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. extractionthe whole was extracted with diethylether
  3. washThe organic layer was washed with saturated NaHCO3 aqueous solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe compound was used for next reaction without purification

Sources & evidence

ORD record
ord-327ab84d4587430891d651c9838efa5f
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Linked notes

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