Methyl iodide → Ethyl 2-(4-methylphenyl)propanoate

HRID 239073

Reaction equation

HRID 239073 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6])[CH3:2].[C:14]1(C)C=CC(CC(OCC)=O)=CC=1.[Li+].CC([N-]C(C)C)C.CI>C1COCC1.CN1C(=O)N(C)CCC1>[C:10]1([CH3:14])[CH:11]=[CH:12][C:7]([CH:5]([CH3:6])[C:4]([O:3][CH2:1][CH3:2])=[O:13])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 84175Ethyl p-tolylacetateHCID 99643Benzeneacetic acid, alpha-methyl-, ethyl esterHCID 2724682Lithium diisopropylamide

Product 1

HCID 11070524Ethyl 2-(4-methylphenyl)propanoateYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

According to the procedure given for the synthesis of 202, ethyl p-tolylacetate (2.72 g, 15.2 mmol) was reacted with LDA (7.6 mL, 15.25 mmol) and methyl iodide (3.03 g, 21.30 mmol) in anhydrous THF (70 mL) and DMPU (1 mL). After aqueous workup and extraction, the residue was distilled in high vacuo to give 203 (2.5 g, 86.0%) as an oil. Bp 59-63° C./0.2 mmHg. 1H NMR (CDCl3): δ (ppm) 7.18 (d, 2 H, J=8.1), 7.10 (d, 2 H, J=8.1), 4.09 (m, 2 H), 3.67 (q, 1 H, J=7.2), 2.29 (s, 3 H), 1.47 (d, J=7.2 Hz, 3 H), 1.20 (t, J=5.7 Hz, 3 H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm) 174.71, 137.80, 136.63, 129.33, 129.14, 127.36, 60.66, 45.18, 21.05, 18.70, 14.15.

Workup

  1. extractionAfter aqueous workup and extraction
  2. distillationthe residue was distilled in high vacuo

Sources & evidence

ORD record
ord-af776805c1c24e9e8a397dbeb88e47ea
Source dataset
uspto-grants-2014_02
Patent number
US08642653B2

Linked notes

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