2,4,6-Trimethylbenzeneboronic acid → ethyl mesitylacetate

HRID 1892462Notes

Reaction equation

HRID 1892462 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1B(O)O.CCCCCC.[C:19]([O:22][CH2:23][CH3:24])(=[O:21])[CH3:20]>>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH2:20][C:19]([O:22][CH2:23][CH3:24])=[O:21]

Participants

3

Reactant 2

HCID 2921842,4,6-Trimethylbenzeneboronic acidHCID 21226206Ethyl acetate hexane

Product 1

HCID 222429ethyl mesitylacetate

Procedure

Ethyl 2,4,6-trimethylphenylacetate was prepared according to the general experimental method from 2,4,6-trimethylphenylboronic acid (164 mg, 1.00 mmol). After workup by column chromatography (hexane/ethyl acetate, 5:1), ethyl 2,4,6-trimethylphenylacetate is obtained as a colourless liquid in a yield of 62% of theory. 1H NMR (200 MHz, CDCl3): δ=6.89 (s, 2H), 4.10-4.25 (m, 2H), 3.67 (s, 2H), 2.27-2.37 (m, 9H), 1.27 (t, J=7.1 Hz, 3H) ppm; 13C NMR (50 MHz, CDCl3): δ=171.9, 137.4, 136.8, 129.3, 129.2, 61.1, 35.6, 21.3, 20.6, 14.7 ppm; MS (70 eV), m/z (%): 206 (23) [M+], 160, (7), 133 (100), 105 (10) 91 (11); IR (NaCl): ν=2978 (m), 2867 (w), 1732 (s), 1157 (m), 1031 (m) cm−1.

Workup

  1. customEthyl 2,4,6-trimethylphenylacetate was prepared

Sources & evidence

ORD record
ord-79f9d4bd6e9f48349d0cd6b47f8c8fa9
Source dataset
uspto-grants-2013_08
Patent number
US08507688B2

Reaction notes

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