Sodium Hydroxide → 7-Bromonaphthalene-1-carboxylic acid

HRID 1074417Notes

Reaction equation

HRID 1074417 reaction equation
ClCl.[OH-:3].[Na+:4].[Br:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][CH:12]=[C:13]2[C:16](=[O:18])C)=[CH:8][CH:7]=1.[Cl:19][O-].[Na+]>>[Cl:19][O-:3].[Na+:4].[Br:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][CH:12]=[C:13]2[C:16]([OH:18])=[O:3])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24526ChlorineHCID 21709625HCID 21709625, compoundHCID 23665760Sodium Hypochlorite

Product 2

HCID 2527337-Bromonaphthalene-1-carboxylic acidHCID 23665760Sodium Hypochlorite

Conditions

Temperature
0 °C

Procedure

A sodium hypochlorite solution was prepared by introducing chlorine gas (28 g, 0.79 mole) into a solution of NaOH (38 g) in 600 ml of ice water. Solid (7-bromo-1-naphthalenyl)ethanone (19.7 g, 0.079 mole) was added to the stirred sodium hypochlorite solution at 0° C. and then the mixture was heated on a steam bath for 1 hr. The precipitate was removed by filtration. Sodium metabisulfite (10 g) was added to the cooled (0° C.) filtrate. The mixture was adjusted to pH 5 with concentrated HCl. The precipitate was collected and dried. The collected precipitate was crystallized from boiling ethanol by the addition of water to afford 14.7 g (two crops) of the title compound; mp 227-230° C.; NMR (CDCl3) δ 7.55-8.35 (m, 5H), 9.11 (d, J=2 Hz, 1H); IR (CHCl3) 2800, 1672, 1609, 1683, 1668 cm-1.

Workup

  1. temperaturethe mixture was heated on a steam bath for 1 hr
  2. customThe precipitate was removed by filtration
  3. additionSodium metabisulfite (10 g) was added to the
  4. customThe precipitate was collected
  5. customdried
  6. customThe collected precipitate was crystallized
  7. additionby the addition of water

Sources & evidence

ORD record
ord-e0ef84dfac0b4e709baf18fe16619768
Source dataset
uspto-grants-1983_07
Patent number
US04391816

Reaction notes

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