Water → 4-[2-(1-Naphthalenyl)-2-oxoethoxy]-alpha-oxobenzeneacetic acid

HRID 2225843Notes

Reaction equation

HRID 2225843 reaction equation
C[O:2][C:3](=[O:26])[C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)=[O:14])=[CH:7][CH:6]=1.[OH-].[Na+].O>CO.O1CCCC1>[C:15]1([C:13](=[O:14])[CH2:12][O:11][C:8]2[CH:9]=[CH:10][C:5]([C:4](=[O:25])[C:3]([OH:26])=[O:2])=[CH:6][CH:7]=2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 537346144-[2-(1-Naphthalenyl)-2-oxoethoxy]-alpha-oxobenzeneacetic acid methyl ester

Product 1

HCID 190042984-[2-(1-Naphthalenyl)-2-oxoethoxy]-alpha-oxobenzeneacetic acidYield 51.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a hot solution of 4-[2-(1-naphthalenyl)-2-oxoethoxy]-alpha-oxobenzeneacetic acid methyl ester (0.128 g) in methanol (3 mL) and tetrahydrofuran (0.5 mL) was added 1N sodium hydroxide (0.8 mL) followed by water (15 mL). The solvents were removed under reduced pressure, then the solution was acidified with 1N hydrochloric acid (1 mL) and extracted with dichloromethane (1×20 mL, 1×10 mL). The combined organic layers were washed with water, dried (MgSO4) and evaporated and the resulting yellow solid (0.107 g) was crystallized from ethyl acetate-hexane to provide 0.063 g of 4-[2-(1-naphthalenyl)-2-oxoethoxy]-alpha-oxobenzeneacetic acid, mp 141°-143° C.

Workup

  1. customThe solvents were removed under reduced pressure
  2. extractionextracted with dichloromethane (1×20 mL, 1×10 mL)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customthe resulting yellow solid (0.107 g) was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-864c6c94d9864819b88be0dbdc83fe9d
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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