Methanol → Cyclopentyloxy-acetic acid methyl ester

HRID 2085012Notes

Reaction equation

HRID 2085012 reaction equation
[CH:1]1([O:6][CH2:7][C:8]([OH:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:11]1(C)C=CC(S(O)(=O)=O)=CC=1.CO>O>[CH:1]1([O:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 13355021(Cyclopentyloxy)acetic acid

Product 1

HCID 43119654Cyclopentyloxy-acetic acid methyl esterYield 4,424.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a three necks 500 ml flask were introduced, in the following order, 65 g (451 mmol) of (cyclopentyloxy)acetic acid (obtained according to U.S. Pat. No. 4,735,932), 1.4 g of para-toluenesulfonic acid and 280 ml of MeOH. After 6 hours at reflux, the reaction mixture was cooled at room temperature diluted into 300 ml of water and extracted with 300 ml of ether. The organic phase thus obtained was washed twice with water, dried over MgSO4 and concentrated. It was thus obtained 56.9 g of product (yield=80%) having a GC purity of 99%.

Workup

  1. customobtained
  2. temperatureAfter 6 hours at reflux
  3. extractionextracted with 300 ml of ether
  4. customThe organic phase thus obtained
  5. washwas washed twice with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a299cdf592e440998891f3b3b73c5cf4
Source dataset
uspto-grants-2004_04
Patent number
US06720295B2

Reaction notes

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