Methyl chloroformate → Methyl 3-(3,5-dimethylphenyl)prop-2-ynoate

HRID 382901Notes

Reaction equation

HRID 382901 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]#[CH:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[Li]CCCC.Cl[C:17]([O:19][CH3:20])=[O:18].C(=O)(O)[O-].[Na+]>C1COCC1.C(=O)=O.CC(C)=O.C(OCC)C>[CH3:20][O:19][C:17](=[O:18])[C:10]#[C:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[CH:3]=1

Participants

8

Reactant 4

HCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 64326111-Ethynyl-3,5-dimethylbenzeneHCID 178418339Butyllithium

Product 1

HCID 20700477Methyl 3-(3,5-dimethylphenyl)prop-2-ynoate

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 18522661Acetone cardiceSolvent

Procedure

1H NMR(CDCl3) δ7.12 (2H,s), 6.98 (1H,s), 3.00 (1H,s), 2.29 (6H, s). 1-(3,5-dimethylphenyl)acetylene (11.3 g, 86.3 mmol) in dry THF (80 mL) was cooled in dry ice/acetone bath under an argon atmosphere. The n-BuLi (1.6M in hexanes, 65 mL, 104 mmol) was added slowly, followed by methyl chloroformate (11.4 g, 9.4 mL, 121 mmol) addition. The reaction vessel was transferred to an ice/water bath and stirred for 1 h. Saturated sodium bicarbonate solution and ethyl ether were added to the reaction mixture. The organic layer was washed with saturated brine, dried (Na2SO4), and concentrated to give crude 3-(3,5-dimethylphenyl)propynoic acid methyl ester which was used for next step.

Workup

  1. customThe reaction vessel was transferred to an ice/water bath
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-69b434c806584f338615f804a255fcf1
Source dataset
uspto-grants-2001_10
Patent number
US06310247B1

Reaction notes

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