Potassium Carbonate → HCID 18476219, compound

HRID 2187643Notes

Reaction equation

HRID 2187643 reaction equation
[OH:1][C:2]1[C:3]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][C:5]2[C:10]([C:11]=1[CH3:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:17](I)[CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:12][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:13]([O:15][CH3:16])=[O:14])[C:2]=1[O:1][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 336431-Iodopropane2×HCID 18476321HCID 18476321, compound

Product 1

HCID 18476219HCID 18476219, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

3-Hydroxy-4-methyl-2-naphthoic acid was prepared according to a literature procedure (Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 2 (1979), 786; Farmaco, Ed. Sci. 33 (1978), 822) and esterified with methanol using standard conditions to give methyl 3-hydroxy-4-methyl-2-naphthoate. A suspension of 300 mg (1.39 mmol) of this ester, 263 mg (1.55 mmol) propyl iodide, and 215 mg (1.55 mmol) of dry potassium carbonate in 60 ml of absolute butanone was stirred at 60° C. for 5 days. After addition of the same amounts of propyl iodide and potassium carbonate stirring was continued at 60° C. for another 2 days. The inorganic salts were filtered off, washed with acetone, and together with a small amount of silica gel the filtrate was evaporated to dryness. The remaining powder was applied to column chromatography on silica gel using hexane followed by a hexane/tert.-butylmethylether gradient up to 9:1.

Workup

  1. waitwas continued at 60° C. for another 2 days
  2. filtrationThe inorganic salts were filtered off
  3. washwashed with acetone
  4. customtogether with a small amount of silica gel the filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-6fd0e853aea240c6b6d7dafae9e08715
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

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