Methyl Salicylate → HCID 57939225, compound

HRID 330741Notes

Reaction equation

HRID 330741 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 mmol) 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-a5000d5875934389b6e4667f7438b2d9
Source dataset
uspto-grants-2014_11
Patent number
US08877684B2

Reaction notes

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