Hydrochloric Acid → 8-Bromonaphthalene-2-carboxylic acid

HRID 259903Notes

Reaction equation

HRID 259903 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([C:12]([O:14]C)=[O:13])[CH:8]=[CH:7]2.[OH-].[Na+].Cl>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([C:12]([OH:14])=[O:13])[CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12068970Methyl 8-bromo-2-naphthalenecarboxylate

Product 1

HCID 146963788-Bromonaphthalene-2-carboxylic acidYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 5.73 (21.6 mmoles) of 8-bromo-2-naphthoic acid, methyl ester (VIII) in 50.0 mL of ethanol was added 21.6 mL (216 mmoles) of 10N NaOH at room temperature. After 1 hour, an excess of 1N HCl was added. The precipitate was collected, washed with 1N HCl and air dried to give 5.40 g (yield: 99%) of 8-bromo-2-naphthoic acid; 1H-NMR: δ13.35 (bs, 1H), 8.80, (s, 1H), 8.11 (m, 3H), 7.98 (d, J=8.0 Hz, 1H), 7.59 (dd, J=7.2 Hz, 1H).

Workup

  1. customThe precipitate was collected
  2. washwashed with 1N HCl and air
  3. customdried

Sources & evidence

ORD record
ord-560884c43e374075b9eaac9e1779ac28
Source dataset
uspto-grants-1996_06
Patent number
US05523457

Reaction notes

Loading…