[3-(4'-Chloro-4-methylbiphenyl-3-yl)-1,1-dimethylprop-2-ynyloxy]acetic acid → 6-[1-(4'-Chloro-4-methylbiphenyl-3-yl)methylidene]-5,5-dimethyl-[1,4]dioxan-2-one

HRID 1191550Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([C:15]#[C:16][C:17]([CH3:24])([CH3:23])[O:18][CH2:19][C:20]([OH:22])=[O:21])[CH:9]=2)=[CH:4][CH:3]=1>C(#N)C.C(=O)([O-])[O-].[Ag+2]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH:15]=[C:16]3[O:21][C:20](=[O:22])[CH2:19][O:18][C:17]3([CH3:24])[CH3:23])[CH:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Silver carbonate (0.17 g, 0.61 mmol) is added to a solution of [3-(4′-chloro-4-methyl-biphenyl-3-yl)-1,1-dimethylprop-2-ynyloxy]acetic acid (2.1 g, 6.13 mmol) in anhydrous acetonitrile (15 ml) in a microwave vial. The reaction mixture is stirred and heated to 120° C. for 40 minutes under microwave irradiation to give a brown suspension. The mixture is evaporated in vacuo, then diluted with water and extracted with ethyl acetate. The combined organic extracts are dried over anhydrous sodium sulfate, filtered and the filtrate evaporated in vacuo to give 6-[1-(4′-chloro-4-methylbiphenyl-3-yl)methylidene]-5,5-dimethyl-[1,4]dioxan-2-one (1.75 g) as a solid.

Workup

customto give a brown suspension
customThe mixture is evaporated in vacuo
additiondiluted with water
extractionextracted with ethyl acetate
dry with materialThe combined organic extracts are dried over anhydrous sodium sulfate
filtrationfiltered
customthe filtrate evaporated in vacuo

Sources & evidence

ORD record: ord-6a5aac0a0b724decad3c18f3ac7e67a5
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680012B2

Reaction notes

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