Dimethyl Sulfate → HCID 44550983, compound

HRID 2238404Notes

Reaction equation

HRID 2238404 reaction equation
CN(C)[C:3]([S:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([C:16]([O:18]C)=[O:17])[CH:10]=[CH:9]2)=O.[OH-].[K+].COS(OC)(=O)=O>CO>[CH3:3][S:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([C:16]([OH:18])=[O:17])[CH:10]=[CH:9]2

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 44550982HCID 44550982, compound

Product 1

HCID 44550983HCID 44550983, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

A suspension of 158 (6.36 g, 22-mmol) in a mixture of aqueous KOH (5N, 340 mL, 1.7 mol) and MeOH (205 mL) was stirred at reflux for 3 h, then cooled to 5° C. and treated dropwise with Me2SO4 (26 mL. 275 mmol). After stirring at room temperature for a further 4 h the mixture was concentrated to half volume, acidified with dilute aqueous HCl, and the precipitated product was crystallised from EtOAc/hexane to give 6-(methylsulfanyl)-2-naphthoic acid (159) (4.39 g, 91%) as a white solid: mp (MeOH) 231-233° C.; 1H NMR [(CD3)2SO] δ (CO2H not observed) 8.53 (s, 1H), 8.01 (d, J=8.9 Hz, 1H), 7.96 (dd, J=8.6, 1.7 Hz, 1H), 7.90 (d, J=8.7 Hz, 1H), 7.77 (d, J=1.7 Hz, 1H), 7.47 (dd, J=+8.7, 1.9 Hz, 1H), 2.61 (s, 3H). Anal. (C12H10O2S) C, H.

Workup

  1. temperatureat reflux for 3 h
  2. stirringAfter stirring at room temperature for a further 4 h the mixture
  3. concentrationwas concentrated to half volume
  4. customthe precipitated product was crystallised from EtOAc/hexane

Sources & evidence

ORD record
ord-009c2e9a81fb43418ff1db85f8aee721
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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