Water → HCID 59379833, compound

HRID 2353542Notes

Reaction equation

HRID 2353542 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-5397bd4d8d584ef38d1052728c592f23
Source dataset
uspto-grants-2010_07
Patent number
US07749999B2

Reaction notes

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