Water → 2-Naphthylglycolic acid

HRID 388250

Reaction equation

HRID 388250 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[O:12].[OH-].[Na+].C(O)[C@H]1[O:21][C@@H:20]2[O:22][C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@H]1[C@H](O)[C@H]2O)O[C@@H]8CO)O[C@@H]7CO)O[C@@H]6CO)O[C@@H]5CO)O[C@@H]4CO)O[C@@H]3CO.O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)(Cl)Cl>[OH:12][CH:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[C:20]([OH:22])=[O:21]

Participants

7

Reactant 4

HCID 962WaterHCID 62012-NaphthalenecarboxaldehydeHCID 14798Sodium HydroxideHCID 444041beta-Cyclodextrin

Product 1

HCID 111381432-Naphthylglycolic acidYield 4,209.8%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 2-naphthaldehyde (2.0 g, 1.0 eq), benzyltriethylammonium chloride (BTEAC) (0.13 g), and 50% aqueous NaOH (2.3 mL), and β-cyclodextrin (0.10 g) in chloroform (10 mL) was heated at 55° C. for 12 hours. The mixture was then poured into water and the solution washed with EtOAc. The aqueous layer was then acidified to pH 1 by dropwise addition of HCl (conc.). This was extracted with EtOAc, dried over Na2SO4, filtered and concentrated under reduced pressure to yield a yellow oil (0.75 g, 29%) that was not further purified.

Workup

  1. washthe solution washed with EtOAc
  2. additionThe aqueous layer was then acidified to pH 1 by dropwise addition of HCl (conc.)
  3. extractionThis was extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-88020106d14d4aa3a2087b5944e3fbfc
Source dataset
uspto-grants-2013_02
Patent number
US08377930B2

Linked notes

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