Phenol → HCID 13776066, compound

HRID 2082546Notes

Reaction equation

HRID 2082546 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]1[O:12][CH:9]1[CH:10]=[CH2:11]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:12][CH2:8][CH:9]=[CH:10][CH2:11][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:12][CH2:8][CH:9]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:10]=[CH2:11]

Participants

6

Reactant 2

HCID 996Phenol2×HCID 13586Vinyloxirane

Product 2

HCID 13776066HCID 13776066, compoundHCID 54122369HCID 54122369, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Tetrakis(triphenylphosphine)palladium (0.4 g, 0.35 mmol) and phenol were dissolved in 70 mL THF and the solution was cooled to 0° C. Butadiene monoxide (5.5 mL, 50 mmol) was then added, and the reaction was allowed to warm to room temperature. After 2 hours at room temperature, GLC analysis indicated that phenol was no longer present, and that two products were obtained in a 1:4 ratio (1-hydroxy-4-phenoxy-but-2-ene: 4-hydroxy-3-phenoxy-but-1-ene). The solvent and excess butadiene monoxide were removed at reduced pressure, and the residue was chromatographed on silica gel (ether:hexane; 1:1 eluant) giving pure samples of each product in a combined yield of 91%.

Workup

  1. temperatureto warm to room temperature

Sources & evidence

ORD record
ord-3a485b6169c440718dc3018892c9fd10
Source dataset
uspto-grants-1993_02
Patent number
US05189199

Reaction notes

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