3-Hydroxybenzaldehyde → HCID 86742645, compound

HRID 414849Notes

Reaction equation

HRID 414849 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[OH:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O.[C:23](=[O:26])([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].[CH3:37][C:38](C)=[O:39]>>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[CH2:3][O:14][C:15]1[CH:16]=[C:17]([CH2:18][C:23](=[O:26])[CH2:37][CH2:38][OH:39])[CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 6

HCID 1013-HydroxybenzaldehydeHCID 180AcetoneHCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 86742645HCID 86742645, compound

Procedure

A mixture of 2-chloromethyl quinoline hydrochloride (10 g, 47 mmol), 3-hydroxybenzaldehyde (6.3 g, 52 mmol), powdered potassium carbonate (14.5 g, 105 mmol), catalytic amounts of cesium carbonate (1.5 g) and sodium iodide (0.7 g) in dry acetone (150 ml) was refluxed for 14 hours. The solid residue was filtered off, and the filtrate was concentrated and dissolved in ethyl acetate. The organic solution was washed successively with 10% NaOH solution water and brine and then dried over MgSO4. All volatiles were removed to leave a yellowish solid weighing 14.8 g. This was recrystallized from hexanes-ethanol mixture to obtain 4-(3-(2-quinolinylmethoxy)phenyl-4-hydroxy-2-butanone as off-white crystals (11.8 g), mp 116°-9° C.

Workup

  1. temperaturewas refluxed for 14 hours
  2. filtrationThe solid residue was filtered off
  3. concentrationthe filtrate was concentrated
  4. dissolutiondissolved in ethyl acetate
  5. washThe organic solution was washed successively with 10% NaOH solution water and brine
  6. dry with materialdried over MgSO4
  7. customAll volatiles were removed
  8. customto leave a yellowish solid
  9. customThis was recrystallized from hexanes-ethanol mixture

Sources & evidence

ORD record
ord-8ff7e06c6ebc46988e672ef492ee9e34
Source dataset
uspto-grants-1988_12
Patent number
US04794188

Reaction notes

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