Benzyl Alcohol → Benzyl 2,2-dimethylbut-3-ynoate

HRID 1964470Notes

Reaction equation

HRID 1964470 reaction equation
[CH3:1][C:2]([CH3:8])([C:6]#[CH:7])[C:3]([OH:5])=[O:4].[CH2:9](O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[CH3:1][C:2]([CH3:8])([C:6]#[CH:7])[C:3]([O:5][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:4]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 139056472,2-Dimethylbut-3-ynoic acid

Product 1

HCID 44784894Benzyl 2,2-dimethylbut-3-ynoateYield 63,227.602%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2,2-dimethylbut-3-ynoic acid (87.7 g, 0.782 mmol) and benzyl alcohol (114.6 g, 0.938 mol) in dichloromethane (800 mL) was added DCC (193.5 g, 0.938 mmol) at −20° C. The reaction mixture was stirred at room temperature overnight and then the solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel (2% ethyl acetate in petroleum ether as eluant) to afford benzyl 2,2-dimethylbut-3-ynoate (100 g, 59% yield). 1H NMR (CDCl3, 400 MHz) δ 7.37-7.36 (m, 5 H), 5.19 (s, 2 H), 2.28 (s, 1 H), 1.52 (s, 6 H).

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe residue was purified by chromatography on silica gel (2% ethyl acetate in petroleum ether as eluant)

Sources & evidence

ORD record
ord-8bd113de2a994fe6b0ce09a8e3c5c41e
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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