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51765-22-1

Phenol, 3-[(1E)-3-hydroxy-1-propen-1-yl]- synthesis

3synthesis methods
66417-46-7 Synthesis
2-Propenoic acid, 3-(3-hydroxyphenyl)-, Methyl ester, (2E)-

66417-46-7
16 suppliers
$435.00/1g

Phenol, 3-[(1E)-3-hydroxy-1-propen-1-yl]-

51765-22-1
1 suppliers
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Yield:51765-22-1 78%

Reaction Conditions:

Stage #1: trans-3-(3-hydroxyphenyl)acrylic acid methyl esterwith diisobutylaluminium hydride in toluene at 0; for 3.5 h;
Stage #2: with methanol in toluene;

Steps:

3.b

b) 3- (3-Hvdroxvpropenvl) phenol (3b); 3a (2.5 g, 14 mmol) is placed in 35 ml of toluene under nitrogen at 0°C and then 29 ml of a solution of DIBAL (1.5M in toluene) are run in dropwise. After stirring at this temperature for 3 h 30 min, the reaction medium is neutralized with methanol and then filtered through celite. After having concentrated the filtrate to dryness, the residue obtained is purified by flash chromatography on silica (CH2CI2-EtOAc : 70-30) and 1.65 g of 3b are recovered in the form of a solid (yield = 78%). TLC Merck silica gel 60 F 254, petroleum ether-EtOAc: 70-30, Rf = 0.53

References:

WO2005/80354,2005,A1 Location in patent:Page/Page column 23-24