Phenol → HCID 18362102, compound

HRID 1857829Notes

Reaction equation

[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:10]=[C:11]([CH:19](OC(=O)C)[C:20]([Cl:23])([Cl:22])[Cl:21])[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13].[O-]C1C=CC=CC=1>O1CCCC1.CCOCC.O>[CH2:10]=[C:11]([CH:19]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:20]([Cl:21])([Cl:23])[Cl:22])[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

Phenol (2.0 g) in 15 ml of tetrahydrofuran (THF) was slowly added to sodium hydride (1.0 g, 60% in oil) suspended in 5 ml THF at 0° C. Fifteen minutes later, 3.0 g of butyl 2-methylene-3-acetoxy-4,4,4-trichlorobutyrate (crude, GC: 86%) in 10 ml THF was slowly dropped into the phenoxide solution. The reaction was stirred at 0° C. for 3 hours and then permitted to warm to room temperature. The reaction was worked up by addition of 50 ml of water and 50 ml of ether. The organic layer was separated and the solvents were removed by vacuum. The resulting yellow oil was transferred to an alumina column and the product was eluted out with hexanes. A slightly yellow oil was obtained after removal of the hexanes, 3.1 g. The product was confirmed by NMR spectroscopy to be butyl 2-methylene-3-phenoxy-4,4,4-trichlorobutyrate.

Workup

temperatureto warm to room temperature
customThe organic layer was separated
customthe solvents were removed by vacuum
washthe product was eluted out with hexanes
customA slightly yellow oil was obtained
customafter removal of the hexanes, 3.1 g

Sources & evidence

ORD record: ord-7d9e934bbe1348a693e14400cdbc15c7
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06147251

Reaction notes

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