Water → HCID 59379833, compound

HRID 598710Notes

Reaction equation

HRID 598710 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][O:6][C:7](=[O:11])[C:8](Cl)=[O:9].[C:12]1([OH:22])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.O>C(Cl)Cl>[CH3:5][O:6][C:7](=[O:11])[C:8]([C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([OH:22])=[CH:13][CH:14]=1)=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 70051-NaphtholHCID 79846Methyl chloroglyoxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 59379833HCID 59379833, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of AlCl3 (1.11 g, 8.3 mmol) in 50 mL DCM, methylchloroglyoxylate (1.02 g, 8.3 mmol) was added. The resulting solution was stirred for 5 min., after which naphthalen-1-ol (1 g, 6.9 mmol) was added. After stirring for 2 hrs at room temperature, water was added and the phases were separated, after which the organic layer was washed with water and dried over MgSO4. The residue obtained after evaporation of the organic solvent was purified by column chromatography (10-30% EtOAc/Hex), to afford the target compound in 38% yield. Calculated mass=230. Observed mass=231.

Workup

  1. additionwas added
  2. stirringAfter stirring for 2 hrs at room temperature
  3. customthe phases were separated
  4. washafter which the organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. customThe residue obtained
  7. customafter evaporation of the organic solvent
  8. customwas purified by column chromatography (10-30% EtOAc/Hex)
  9. customto afford the target compound in 38% yield

Sources & evidence

ORD record
ord-a734bb055e34429ab4fabddf165fecfc
Source dataset
uspto-grants-2011_03
Patent number
US07897599B2

Reaction notes

Loading…