Water → HCID 9932554, compound

HRID 1610991Notes

Reaction equation

HRID 1610991 reaction equation
[OH:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:11](=[O:14])([O-])[O-:12].[K+].[K+].[Cl:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20]Cl.O>CCO>[Cl:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20][O:1][C:2]1[C:9]([O:10][CH2:20][C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[Cl:17])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]([OH:5])[C:11]([OH:12])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 119062-Chlorobenzyl chlorideHCID 905792,3-Dihydroxybenzaldehyde

Product 1

HCID 9932554HCID 9932554, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred slurry of 2,3-dihydroxybenzaldehyde (6.91 g, 50.0 mmol) and potassium carbonate (17.2 g, 125 mmol) in EtOH (60 mL) at room temperature under argon was added 2-chlorobenzyl chloride (15 mL, 120 mmol). The reaction mixture was heated to reflux for 16 h, then cooled and poured into water (150 mL). The resulting solids were collected, washed with water, air-dried and recrystallized from methanol to give the title compound as white needles (16.28 g, 71% yield), mp 98-100° C. LC/MS gave the correct molecular ion [(M+H)+=387] for the desired compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 16 h
  3. temperaturecooled
  4. customThe resulting solids were collected
  5. washwashed with water
  6. customair-dried
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-f6140c0a46014f769b645fb2bc1146e7
Source dataset
uspto-grants-2006_01
Patent number
US06984645B2

Reaction notes

Loading…