Acetone → HCID 10970592, compound

HRID 742099Notes

Reaction equation

HRID 742099 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14]([OH:16])[C:13]2[C:8](=[C:9]([Br:21])[CH:10]=[CH:11][C:12]=2[O:17][CH:18]([CH3:20])[CH3:19])[CH:7]=1)=[O:5])[CH3:2].[CH3:22]C(C)=O.COS(OC)(=O)=O>N>[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14]([O:16][CH3:22])[C:13]2[C:8](=[C:9]([Br:21])[CH:10]=[CH:11][C:12]=2[O:17][CH:18]([CH3:20])[CH3:19])[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 15341855HCID 15341855, compound

Product 1

HCID 10970592HCID 10970592, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

To a solution of 4.92 g (13.9 mmol) ethyl-8-bromo-4-hydroxy-5-isopropoxy-2-naphthoate in 150 mL acetone 4.80 g (34.8 mmol) K2CO3 and dropwise 4.90 g (38.7 mmol) dimethylsulfate at room temperature were added. Subsequently the reaction mixture was refluxed for 10 h and after that 60 mL of concentrated ammonia was added. Solvent was removed under vacuum and the residue was partitioned between water and dichloromethane. The combined organic phases were washed three times with 2N NaOH solution and two times with water. The organic phase was dried (MgSO4) and concentrated under vacuum. The residue was recrystallized from diethylether to give 5.00 g (99%) ethyl-8-bromo-5-isopropoxy-4-methoxy-2-naphthoate as colorless needles (m.p. 62° C.).

Workup

  1. temperatureSubsequently the reaction mixture was refluxed for 10 h
  2. customSolvent was removed under vacuum
  3. customthe residue was partitioned between water and dichloromethane
  4. washThe combined organic phases were washed three times with 2N NaOH solution and two times with water
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated under vacuum
  7. customThe residue was recrystallized from diethylether

Sources & evidence

ORD record
ord-a467df2b503442df947ad4edbb2db1f0
Source dataset
uspto-grants-1996_09
Patent number
US05552550

Reaction notes

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