4-Hydroxybenzyl Alcohol → HCID 15203943, compound

HRID 219310Notes

Reaction equation

HRID 219310 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:16](Br)[C:17]#[CH:18]>C(#N)C.C1(C)C=CC=CC=1>[CH2:18]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1)[C:17]#[CH:16]

Participants

6

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 7842Propargyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 15203943HCID 15203943, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-hydroxyl-benzyl alcohol 13 (2.5 g, 20 mmol) in acetonitrile (50 mL), K2CO3 (3.96 g, 200 mol %) was added at room temperature (see Scheme 4). After stirring for 1 h, the mixture was treated dropwise with an 80 wt % solution of propargyl bromide in toluene (3.27 g, 110 mol %) and the reaction mixture was heated to 50° C. for 48 h, cooled, filtered and concentrated under vacuum. The residue was purified by flash chromatography using an eluent of 100% to 30% hexane in AcOEt. Evaporation of the collected fractions gave propargyl ether 14 as a yellow liquid (3.12 g, 95.5%): 1H NMR (CDCl3) δ (ppm): 7.28 (d, 2H, Ph-H), 6.96 (d, 2H, Ph-H), 4.69 (d, 2H, PhCH2), 4.57 (s, 2H, CCH2O), 2.54 (t, 1H, OH), 2.39 (s, 1H, CH); 13C NMR (CD3OD) δ (ppm): 157.4, 134.53, 128.97, 115.34, 78.97, 76.04, 65.10, 56.24. Anal. Calcd for C10H10O2: C, 74.07; H, 6.17. Found: C, 73.64; H, 6.03.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by flash chromatography
  5. customEvaporation of the collected fractions

Sources & evidence

ORD record
ord-62e13c3f9ad541509c52cbee63384c46
Source dataset
uspto-grants-2012_06
Patent number
US08198364B2

Reaction notes

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