2-Phenylethanol → HCID 21036281, compound

HRID 1789645Notes

Reaction equation

HRID 1789645 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]([CH3:14])=[CH:10][C:11]([OH:13])=[O:12].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[CH2:40](O)[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>O1CCCC1.CN(C)C1C=CN=CC=1>[CH2:40]([O:12][C:11](=[O:13])/[CH:10]=[C:9](/[C:3]1[CH:4]=[CH:5][C:6]([OH:8])=[CH:7][C:2]=1[OH:1])\[CH3:14])[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

7

Reactant 4

HCID 60542-PhenylethanolHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 66933108HCID 66933108, compound

Product 1

HCID 21036281HCID 21036281, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

To a 0° C. solution of 9.7 g (0.050 mol) of 3-(2,4-dihydroxyphenyl)but-2-enoic acid in 500 mL of anhydrous tetrahydrofuran (THF) is added 10.3 g (0.050 mol) of 1,3-dicyclohexylcarbodiimide (DCC). After stirring for 10 min, 6.8 g (0.050 mol) of 1-hydroxybenzotriazole (HOBt), 5.5 g (0.045 mol) of phenethyl alcohol and 1.1 g (0.009 mol) of 4-(dimethylamino)pyridine (DMAP) is added and stirred at 0° C. for 1 h, warmed to 22° C. and stirred for an additional 72 h. The mixture is cooled to 0° C., filtered and the solvent is removed under vacuum. The residue is diluted with ethyl acetate and washed three times with saturated sodium bicarbonate, followed by 10% citric acid and brine. The organic layer is dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to give (E)-3-(2,4-dihydroxyphenyl)-but-2-enoic acid phenethyl ester as a yellow oil that is purified by flash chromatography.

Workup

  1. stirringstirred at 0° C. for 1 h
  2. stirringstirred for an additional 72 h
  3. temperatureThe mixture is cooled to 0° C.
  4. filtrationfiltered
  5. customthe solvent is removed under vacuum
  6. additionThe residue is diluted with ethyl acetate
  7. washwashed three times with saturated sodium bicarbonate
  8. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-29931067ae7f4dd5b8eb596caeb473e3
Source dataset
uspto-grants-2006_07
Patent number
US07071151B2

Reaction notes

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