Methyl Salicylate → HCID 57939225, compound

HRID 218285Notes

Reaction equation

HRID 218285 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([O-])([O-])=O.[K+].[K+].I[CH2:19][CH2:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>CN(C=O)C>[CH2:19]([O:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[CH2:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 4133Methyl SalicylateHCID 11430Potassium CarbonateHCID 14428358HCID 14428358, compound

Product 1

HCID 57939225HCID 57939225, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

88 mg of 28 (578 μmol) and 77 mg of K2CO3 (557 μmol) are added to 140 mg of 13 (500 μmol) in anhydrous DMF (2 mL). After reaction for 8 hours at 90° C., the reaction medium is concentrated, taken up in DCM and then washed with water. 137 mg of a yellow oil are obtained, and are chromatographed on silica gel in pentane/ethyl acetate (40/1). 100 mg of a yellow oil are isolated, i.e. a yield of 66%.

Workup

  1. customAfter reaction for 8 hours at 90° C.
  2. concentrationthe reaction medium is concentrated
  3. washwashed with water

Sources & evidence

ORD record
ord-ea3718c15080468e986d2f1cbcdaf176
Source dataset
uspto-grants-2012_06
Patent number
US08198420B2

Reaction notes

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