Benzyl Alcohol → Benzyl 4-pentynoate

HRID 1377922Notes

Reaction equation

HRID 1377922 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][CH2:3][C:4]#[CH:5].C(Cl)(=O)C(Cl)=O.[CH2:14](O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClCCl.CN(C=O)C>[CH2:14]([O:6][C:1](=[O:7])[CH2:2][CH2:3][C:4]#[CH:5])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 224644-Pentynoic acidHCID 65578Oxalyl chloride

Product 1

HCID 561097Benzyl 4-pentynoateYield 134.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution in dichloromethane (25 mL) containing a few drops DMF of 4-pentynoic acid (2.49 g, 23.4 mmol) was added oxalyl chloride (2.2 mL, 25 mmol). The reaction mixture was stirred for 1.5 hours and benzyl alcohol (3.9 mL, 38 mmol) was added via syringe. The reaction mixture was stirred for 6 hours and then was extracted with saturated aqueous sodium carbonate. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give 4-pentynoic acid benzyl ester (5.94 g) as a yellow liquid.

Workup

  1. stirringThe reaction mixture was stirred for 6 hours
  2. extractionwas extracted with saturated aqueous sodium carbonate
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e3eb54c93f74cee80fa5b9de70512a9
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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