Hydrochloric Acid → HCID 22246671, compound

HRID 890679Notes

Reaction equation

HRID 890679 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][C:20](=[O:23])[CH2:21][CH3:22].Cl.C([O-])(O)=O.[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11](/[CH:12]=[C:21](\[CH3:22])/[C:20](=[O:23])[CH3:19])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6569Methyl Ethyl KetoneHCID 806713-Benzyloxy-4-methoxybenzaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 22246671HCID 22246671, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of commercially available 3-benzyloxy-4-methoxybenzaldehyde (34 g, 0.14 mol, 1 eq) and 2-butanone (50 mL, 0.56 mol, 4 eq) in dry THF (50 mL) was cooled to −4° C. Hydrogen chloride gas was passed through the well-stirred solution for several minutes, and the reaction mixture was capped and stored at −4° C. for 16 h. The mixture was poured into a well stirred solution of ice-cold saturated sodium bicarbonate (NaHCO3) (about 2 L). If necessary, the pH was adjusted to >7 with sat. NaHCO3, and the mixture was extracted with EtOAc (3×300 mL).

Workup

  1. customthe reaction mixture was capped
  2. additionThe mixture was poured into a well
  3. extractionthe mixture was extracted with EtOAc (3×300 mL)

Sources & evidence

ORD record
ord-4c5f7f779e3742878484d1aa9fa4613e
Source dataset
uspto-grants-2006_02
Patent number
US06998416B2

Reaction notes

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