Water → 1-Naphthylglycolic acid

HRID 1251617Notes

Reaction equation

HRID 1251617 reaction equation
[C:1]1([CH:11]=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl-].[Li+].[OH-:15].[K+].[CH:17](Br)(Br)Br.[OH2:21]>>[C:1]1([CH:11]([OH:12])[C:17]([OH:21])=[O:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 962WaterHCID 5558BromoformHCID 61951-NaphthaldehydeHCID 14797Potassium HydroxideHCID 433294Lithium Chloride

Product 1

HCID 2404991-Naphthylglycolic acidYield 79%

Conditions

Temperature
0 °C

Procedure

Under argon atmosphere distilled 1,4-dioxane (100 mL) and distilled water (100 mL) were charged in a two necked-flask in an ice bath. To the flask 1-naphthaldehyde (15.6 g, 0.1 mol), lithium chloride (8.48 g, 0.2 mol) and potassium hydroxide (22.4 g, 0.4 mol) were added. After stirring at 0° C. for 5 minutes, bromoform (25.2 g, 0.1 mol) was added, and stirring was continued for a further 1 hour at the same temperature. Completion of the reaction was ascertained by TLC, and then, water (100 mL) was added to the reaction mixture. After rinsing three times with ether (each 70 mL), pH of the aqueous phase was decreased to 2 with conc. hydrochloric acid under ice cooling. The aqueous phase was subjected to extraction of five times with ether (each 100 mL), and the organic phase thus formed was rinsed once with saturated sodium chloride solution and once with distilled water. The organic phase was dried over anhydrous magnesium sulfate (80 g) and the solvent was distilled off under reduced pressure. The residue was dried under vacuum, and 16.0 g (yield: 79%) of the target compound was obtained. The product, without being purified, was used as the material for optical resolution described below.

Workup

  1. distillationUnder argon atmosphere distilled 1,4-dioxane (100 mL)
  2. distillationdistilled water (100 mL)
  3. additionwere charged in a two necked-flask in an ice bath
  4. stirringstirring
  5. waitwas continued for a further 1 hour at the same temperature
  6. washAfter rinsing three times with ether (each 70 mL), pH of the aqueous phase
  7. extractionThe aqueous phase was subjected to extraction of five times with ether (each 100 mL), and the organic phase
  8. customthus formed
  9. washwas rinsed once with saturated sodium chloride solution and once with distilled water
  10. dry with materialThe organic phase was dried over anhydrous magnesium sulfate (80 g)
  11. distillationthe solvent was distilled off under reduced pressure
  12. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-c7c1a75217e445c4b66844865a955e57
Source dataset
uspto-grants-2002_01
Patent number
US06342636B1

Reaction notes

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