Ethanol → HCID 11687291, compound

HRID 1411181Notes

Reaction equation

HRID 1411181 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH3:9].C(O[O:15][C:16]([CH3:19])(C)C)(C)(C)C.[C]=O.[CH2:22]([OH:24])C>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:22]([O:15][CH2:16][CH3:19])=[O:24]

Participants

5

Reactant 4

HCID 702EthanolHCID 8033Di-tert-butyl peroxideHCID 83682,6-DichlorotolueneHCID 178418416HCID 178418416, compound2×

Product 1

HCID 11687291HCID 11687291, compoundYield 72.2%

Conditions

Temperature
120 °C

Procedure

2,6-Dichlorotoluene (2.4 g), ethanol (46 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl2 (3.8 mg, 1 mol %) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120° C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 84 mg ethyl 2,6-dichlorophenylacetate was obtained by column chromatography, in a yield of 72%. 1HNMR (400 MHz, CDCl3) δ 1.25 (t, J=7.2 Hz, 3H), 4.01 (s, 2H), 4.17 (q, J=7.2 Hz, 2H), 7.14-7.18 (m, 1H), 7.31-7.33 (m, 2H); 13CNMR (100 MHz, CDCl3) δ 14.2, 36.8, 61.1, 128.0, 128.9, 131.4, 136.1, 169.5; HRMS (ESI) calcd. for C10H10Cl2NaO2 [M+Na]: 254.9950. found: 254.9949. The ethyl 2,6-dichlorophenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60° C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 71 mg product 2,6-dichlorophenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 95%.

Workup

  1. additionwas introduced

Sources & evidence

ORD record
ord-98f792771e3d4ce181bfa8078f142b70
Source dataset
uspto-grants-2014_12
Patent number
US08921591B2

Reaction notes

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