Potassium Carbonate → Methyl 2-(cyclohexen-3-yloxy)-5-chlorobenzoate

HRID 1606899Notes

Reaction equation

HRID 1606899 reaction equation
[Cl:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]([OH:12])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:20]1[CH2:25][CH2:24][CH2:23][CH:22]=[CH:21]1>CN(C=O)C>[CH:20]1[CH2:25][CH2:24][CH2:23][CH:22]([O:12][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:11][C:6]=2[C:7]([O:9][CH3:10])=[O:8])[CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl esterHCID 1370573-Bromocyclohexene

Product 1

HCID 14621138Methyl 2-(cyclohexen-3-yloxy)-5-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 18.6 g of methyl 5-chlorosalicylate, 28 g of K2CO3 and 20 g of 3-bromo-cyclohexene in 200 ml of DMF is stirred at 90° C. overnight. The mixture is then poured onto water, extracted with ethylacetate., washed with water, dried over magnesium sulfate and evaporated to dryness to obtain crude product. This is purified by flash chromatography using hexane as the eluent to give pure methyl 2-(cyclohexen-3-yloxy)-5-chlorobenzoate as the first fraction which is used directly in the next step.

Workup

  1. additionThe mixture is then poured onto water
  2. extractionextracted with ethylacetate
  3. wash, washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customto obtain crude product
  7. customThis is purified by flash chromatography

Sources & evidence

ORD record
ord-2524a4791e10452faff7b1b3f73374b4
Source dataset
uspto-grants-1989_09
Patent number
US04863921

Reaction notes

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