HCID 11832841, compound → HCID 13454956, compound

HRID 1904091Notes

Reaction equation

HRID 1904091 reaction equation
[Br:1][C:2]1[C:11]([O:12]C)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:14]([OH:16])=[O:15]>C(O)(=O)C.Br>[Br:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:14]([OH:16])=[O:15]

Participants

4

Reactant 1

HCID 11832841HCID 11832841, compound

Product 1

HCID 13454956HCID 13454956, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A mixture of 5-bromo-6-methoxy-1-naphthalenecarboxylic acid (33.35 g, 0.11 moles, described in example 1b) in glacial acetic acid (460 ml) and 47% aqueous HBr (417 ml) was heated at reflux for 9 hr. The resulting precipitate was collected, washed with water and dried over P2O5 under reduced pressure. The precipitate was recrystallized from ethanol-water to give 21.45 g of 5-bromo-6-hydroxy-1-naphthalenecarboxylic acid; mp>225° C., NMR (DMSO-d6) δ8.0 (m, 5H), 11.0 (broad, 1H), 12.6 (broad, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 9 hr
  3. customThe resulting precipitate was collected
  4. washwashed with water
  5. dry with materialdried over P2O5 under reduced pressure
  6. customThe precipitate was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-ed0d400d66304531a0f42757806fc191
Source dataset
uspto-grants-1984_03
Patent number
US04439617

Reaction notes

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