Water → Methyl 6-(Hydroxymethyl)-2-naphthoate

HRID 463034

Reaction equation

HRID 463034 reaction equation
C([O:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[CH:10]=[CH:9]2)(=O)C.C([O-])([O-])=O.[K+].[K+].O>CO>[OH:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[CH:10]=[CH:9]2

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 15589961Methyl 6-Acetoxymethyl-2-naphthoate

Product 1

HCID 11127663Methyl 6-(Hydroxymethyl)-2-naphthoateYield 100.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.9 g (3.49 mmol) of methyl 6-acetoxymethyl-2-naphthoate in 100 mL of MeOH was added 0.5 g (3.62 mmol) of K2CO3 and 1 mL of H2O. The mixture was stirred at room temperature for 30 min before being evaporated to dryness. The residue was taken up in 50 mL of EtOAc and 30 mL of H2O. The organic layer was dried (Na2SO4) and evaporated to give 0.76 g (100% yield) of methyl 6-hydroxymethyl-2-naphthoate as white crystals: mp 123°-124° C.; IR (mull) 3250, 1720, 1300, 1200, 1130, 1100, 1040, 1020, 920, 900, 840, 820, 760 cm-1 ; 1H NMR (CDCl3) δ2.13 (s, 1, OH), 3.98 (s, 3, CO2CH3), 4.88 (s, 2, CH2OH), 7.3-8.7 (m, 6, ArH); MS calcd for C13H12O3 216.0786, found 216.0787.

Workup

  1. custombefore being evaporated to dryness
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-09c9d1179af345c1999fa29104c63438
Source dataset
uspto-grants-1985_05
Patent number
US04518609

Linked notes

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