Acetone → HCID 67087007, compound

HRID 2365573Notes

Reaction equation

HRID 2365573 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5]2.C([O-])([O-])=[O:17].[K+].[K+].[CH3:22][C:23]([CH3:25])=[O:24]>>[CH3:15][O:14][C:12]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([O:1][CH2:22][C@@H:23]([OH:24])[CH2:25][OH:17])[CH:3]=2)[CH:8]=1)=[O:13]

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 390995Methyl 6-hydroxy-2-naphthoate

Product 1

HCID 67087007HCID 67087007, compound

Procedure

To a solution of methyl 6-hydroxy-2-naphthoate (4.55 g, 22.5 mmol) in anhydrous acetone (60 ml) are added S-(−)-glycidol (2.0 g, 27.0 mmol) and K2CO3 (9.3 g, 67.3 mmol). The reaction mixture is heated to reflux for 3 days. The reaction mixture is filtered through Celite™ (filter material) and the filtrate is concentrated in vacuo to afford 6-((S)-2,3-Dihydroxy-propoxy)-naphthalene-2-carboxylic acid methyl ester as a white solid; 1H NMR (DMSO-d6): 3.49 (2H, t, J=6.0 Hz), 3.85-3.88 (1H, m), 3.89 (3H, s), 4.02 (1H, dd, J=9.9, 6.0 Hz), 4.16 (1H, dd, J=9.9, 4.0 Hz), 4.73 (1H, t, J=6.0 Hz), 5.04 (1H, d, J=5.2 Hz), 7.26 (1H, dd, J=9.0, 2.0 Hz), 7.41 (1H, d, J=2.0 Hz), 7.88-7.94 (2H, m), 8.04 (1H, d, J=9.0 Hz), 8.55 (1H, s).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 3 days
  3. filtrationThe reaction mixture is filtered through Celite™ (filter material)
  4. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-3d348f6d4ece4871ae525e5dd87cfbe3
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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