Sodium Hydroxide → HCID 19004489, compound

HRID 2225751Notes

Reaction equation

HRID 2225751 reaction equation
C[O:2][C:3](=[O:24])[C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)=[CH:7][CH:6]=1.[OH-].[Na+]>CO.O1CCCC1>[CH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:4](=[O:23])[C:3]([OH:24])=[O:2])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53866524HCID 53866524, compound

Product 1

HCID 19004489HCID 19004489, compoundYield 56.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[(2-naphthalenyl)methoxy]-alpha-oxobenzeneacetic acid methyl ester (0.58 g) in methanol (3 mL) and tetrahydrofuran (8 mL) was treated with 1N sodium hydroxide (2.0 mL) and a white precipitate formed immediately. After 5 minutes, the reaction mixture was concentrated, the residue was acidified with excess hydrochloric acid and partitioned between dichloromethane (100 mL) and water (10 mL). The organic layer was dried (MgSO4) and concentrated. The resulting residue was crystallized from dichloromethane-hexane-tetrahydrofuran to give 0.315 g of 4-[(2-naphthalenyl)methoxy]-alpha-oxobenzeneacetic acid, mp 145°-146° C.

Workup

  1. customa white precipitate formed immediately
  2. concentrationthe reaction mixture was concentrated
  3. custompartitioned between dichloromethane (100 mL) and water (10 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customThe resulting residue was crystallized from dichloromethane-hexane-tetrahydrofuran

Sources & evidence

ORD record
ord-4f4ba7d698534d7ba037966183717d11
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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