Water → Methyl 3-hydroxy-1-(methoxymethoxy)-2-naphthoate

HRID 488680Notes

Reaction equation

HRID 488680 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]([OH:15])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[OH:16])=[O:4].C(N(CC)CC)C.[CH3:24][O:25][CH2:26]Cl.O>CN(C=O)C>[OH:15][C:14]1[C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:6]([O:16][CH2:24][O:25][CH3:26])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 8471TriethylamineHCID 450935251,3-Dihydroxy-2-naphthoic acid methyl ester

Product 1

HCID 22271918Methyl 3-hydroxy-1-(methoxymethoxy)-2-naphthoateYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,3-dihydroxy-2-naphthoic acid methyl ester 109 mg (0.53 mmol) in DMF (2 mL) was added triethylamine (200 μL, 1.43 mmol) and chloromethyl methyl ether (MOMCl) (125 μL, 1.65 mmol). The mixture was stirred at ambient temperature for 16 hours, poured into water (10 mL) and extracted with diethyl ether (2×5 mL). The combined ether layers were washed with 1M HCl (1×3 mL), brine (1×5 mL), dried (MgSO4), filtered, and concentrated under reduced pressure to an oil. The oil was purified on silica gel eluting with 20% ethyl acetate/hexanes to provide the titled compound (83 mg, 60%).

Workup

  1. extractionextracted with diethyl ether (2×5 mL)
  2. washThe combined ether layers were washed with 1M HCl (1×3 mL), brine (1×5 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to an oil
  6. customThe oil was purified on silica gel eluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1060d76afbc2406bb7b9b3cd39524762
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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