Acetic Acid → 1-Methyl-2-pentyl-cyclopentanol

HRID 928898Notes

Reaction equation

HRID 928898 reaction equation
C[Mg]Cl.[CH2:4]([CH:9]1[CH2:13][CH2:12][CH2:11][C:10]1=[O:14])[CH2:5][CH2:6][CH2:7][CH3:8].[C:15](O)(=O)C.O>O1CCCC1.C1(C)C=CC=CC=1>[CH3:15][C:10]1([OH:14])[CH2:11][CH2:12][CH2:13][CH:9]1[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 209592-Pentylcyclopentan-1-oneHCID 178418332HCID 178418332, compound

Product 1

HCID 1181163251-Methyl-2-pentyl-cyclopentanolYield 59.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
7.5 °C

Procedure

A 3-L reaction flask was charged with methylmagnesium chloride (MeMgCl) solution in tetrahydrofuran (THF) (800 mL, 2.4 mol) and THF (500 mL). The reaction flask was cooled to 5-10° C. 2-Pentyl-cyclopentanone (370 g, 2.4 mol) (prepared as above in EXAMPLE I) was fed into the reaction mixture over an hour. The reaction was aged for 4 hours and then neutralized with acetic acid (CH3COOH) (160 g) while the temperature was maintained at 5-10° C. The reaction mixture was poured into H2O (3 L) and toluene (1 L). The organic layer was separated and fractional distilled to afford 1-methyl-2-pentyl-cyclopentanol (245 g) having a boiling point of 150-152° C. at 3 mmHg.

Workup

  1. temperaturewas maintained at 5-10° C
  2. customThe organic layer was separated
  3. distillationfractional distilled

Sources & evidence

ORD record
ord-7fe5ae9d0bfd4d18bc3227099ad0c0de
Source dataset
uspto-grants-2016_03
Patent number
US09290718B2

Reaction notes

Loading…