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

HRID 1032832Notes

Reaction equation

HRID 1032832 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-bromocyclohexene 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. washwashed 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-dd01bbe189b84b9cb775d1c5c35c82e4
Source dataset
uspto-grants-1990_09
Patent number
US04959485

Reaction notes

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