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

HRID 1263298Notes

Reaction equation

HRID 1263298 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-6c92616a6bc54a5b81598092ad326f8b
Source dataset
uspto-grants-1984_06
Patent number
US04456618

Reaction notes

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