2-Heptanol → Cyclopropanecarboxylic acid 1-methyl-hexyl ester

HRID 61340

Reaction equation

HRID 61340 reaction equation
[CH3:1][CH:2]([OH:8])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH:9]1([C:12](O)=[O:13])[CH2:11][CH2:10]1>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH3:1][CH:2]([O:8][C:12]([CH:9]1[CH2:11][CH2:10]1)=[O:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 2

HCID 109762-HeptanolHCID 15655Cyclopropanecarboxylic acid

Product 1

HCID 89705028Cyclopropanecarboxylic acid 1-methyl-hexyl esterYield 79.8%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

2-Heptanol (200 g, 1.72 mol) and cyclopropanecarboxylic acid (163 g, 1.90 mol) were added into toluene (500 mL), followed by p-toluenesulfonic acid (3.2 g, 0.0172 mol). The reaction mixture was heated to reflux for 6 hours, cooled to room temperature, and quenched with aqueous sodium bicarbonate (1 L). The reaction mixture was then washed with brine (0.5 L) and dried over sodium sulfate (50 g). The solvent was removed and the reaction mixture was distilled to provide the product cyclopropanecarboxylic acid 1-methyl-hexyl ester (253 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 hours
  3. customquenched with aqueous sodium bicarbonate (1 L)
  4. washThe reaction mixture was then washed with brine (0.5 L)
  5. dry with materialdried over sodium sulfate (50 g)
  6. customThe solvent was removed
  7. distillationthe reaction mixture was distilled

Sources & evidence

ORD record
ord-59cafe26ff9e483eae52495a7a1c2ddb
Source dataset
uspto-grants-2016_09
Patent number
US09441185B2

Linked notes

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