Dimethyl Carbonate → Methyl 7-bromo-3,4-dihydro-2-hydroxy-1-naphthoate

HRID 2289223Notes

Reaction equation

HRID 2289223 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][C:10](=[O:14])[CH2:11]2)=[CH:6][CH:5]=1.[C:15](=O)([O:18]C)[O:16][CH3:17]>>[Br:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][C:10]([OH:14])=[C:11]2[C:15]([O:16][CH3:17])=[O:18])=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 12021Dimethyl Carbonate2×HCID 24758Sodium hydrideHCID 36915747-Bromo-2-tetralone

Product 1

HCID 54708334Methyl 7-bromo-3,4-dihydro-2-hydroxy-1-naphthoate

Procedure

To a refluxing stirred suspension of sodium hydride (5.6 g of 80% in oil, 187 mmoles) in dry dimethyl carbonate (120 ml) under a nitrogen atmosphere was added a solution of 7-bromo-2-tetralone (14 g, 61 mmoles) in dry dimethyl carbonate (60 ml) dropwise over 40 minutes. Refluxing was continued for an additional 45 minutes and then cooled to room temperature. The reaction was carefully quenched with glacial acetic acid, diluted with one volume of water and extracted with ethyl acetate (150 ml). The organic phase was dried over magnesium sulfate, filtered and evaporated under reduced pressure to leave a residue which was purified using silica gel column chromatography eluting with ethyl acetate:hexane (39:7) to give methyl 7-bromo-3,4-dihydro-2-hydroxy-1-naphthoate as a white solid. (15.2 g, 86%).

Workup

  1. temperatureRefluxing
  2. customThe reaction was carefully quenched with glacial acetic acid
  3. additiondiluted with one volume of water
  4. extractionextracted with ethyl acetate (150 ml)
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto leave a residue which
  9. customwas purified
  10. washeluting with ethyl acetate:hexane (39:7)

Sources & evidence

ORD record
ord-3ac8c717bd3649c487e2fb6e7cb2477d
Source dataset
uspto-grants-2000_07
Patent number
US06090941

Reaction notes

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