Water → HCID 15341855, compound

HRID 742098Notes

Reaction equation

HRID 742098 reaction equation
[C:1](/[C:6](=[CH:11]/[C:12]1[CH:17]=[C:16](C(C)C)[CH:15]=[CH:14][C:13]=1[Br:21])/[CH2:7][C:8]([OH:10])=O)([O:3][CH2:4][CH3:5])=[O:2].O.[C:23]([O-])([O-])=O.[K+].[K+].[Na].C(O[C:34](=[O:36])[CH3:35])(=O)C>C(O)C>[CH2:4]([O:3][C:1]([C:6]1[CH:7]=[C:8]([OH:10])[C:17]2[C:12](=[C:13]([Br:21])[CH:14]=[CH:15][C:16]=2[O:36][CH:34]([CH3:23])[CH3:35])[CH:11]=1)=[O:2])[CH3:5]

Participants

7

Reactant 5

HCID 962WaterHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 5360545SodiumHCID 69961466HCID 69961466, compound

Product 1

HCID 15341855HCID 15341855, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

12.9 g (34.8 mmol) (E)-3-carboethoxy-4-(2'-bromo-5'-isopropylphenyl)-3-butenic acid (3) were dissolved in 340 acetic anhydride and heated for 6 h in reflux. After cooling to room temperature, a solution of 200 g ice, 200 g water and 90 g K2CO3 were added. After extraction with dichloromethane, the combined organic layers were dried (MgSO4), filtered and concentrated under reduced pressure. The dried residue was dissolved in a solution of 8.40 g (389 mmol) sodium in 300 mL dry ethanol and stirred for 4 h at room temperature under Ar. The solvent was removed in vacuo and the residue was partitioned between 100 mL dichloromethane and 30 mL 2N HCl-solution. The organic phases were collected, dried (MgSO4) and concentrated under reduced pressure. The residue was recrystallized from isopropanol to give 11.7 g (95%) ethyl-8-bromo-4-hydroxy-5-isopropoxy-2-naphthoate as yellow crystals (m.p. 106° C.).

Workup

  1. temperatureheated for 6 h
  2. temperaturein reflux
  3. extractionAfter extraction with dichloromethane
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe solvent was removed in vacuo
  8. customthe residue was partitioned between 100 mL dichloromethane and 30 mL 2N HCl-solution
  9. customThe organic phases were collected
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-a8a70e2e24c140c0b7ed7b47df8c7ca5
Source dataset
uspto-grants-1996_09
Patent number
US05552550

Reaction notes

Loading…