Benzyl Alcohol → HCID 13198832, compound

HRID 1530153Notes

Reaction equation

HRID 1530153 reaction equation
[Br:1][CH2:2]/[CH:3]=[CH:4]/[CH2:5]Br.[CH2:7]([OH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>[CH2:7]([O:14][CH2:5]/[CH:4]=[CH:3]/[CH2:2][Br:1])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 3

HCID 244Benzyl AlcoholHCID 14798Sodium HydroxideHCID 641245trans-1,4-Dibromo-2-butene

Product 1

HCID 13198832HCID 13198832, compoundYield 47.9%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of trans-1,4-dibromobut-2-ene (20.0 g, 93.5 mmol), benzyl alcohol (10.6 mL, 102.9 mmol), and tetrabutylammonium hydrogensulfate (3.17 g, 9.35 mmol) in dichloromethane (80 mL) were added sodium hydroxide (33.7 g, 841 mmol) in water and the resulting mixture was stirred at room temperature for 24 hours. It was diluted with water and extracted with diethyl ether. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified using flash column chromatography to yield 10.8 g of trans-4-benzyloxy-1-bromo-2-butene; 1H NMR (400 MHz, CDCl3) δ ppm 3.98 (d, 2H, J=7.3 Hz) 4.04 (d, 2H, J=4.4 Hz) 4.54 (s, 2H) 5.82-6.08 (m, 2H) 7.25-7.45 (m, 5H).

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-b50be943fb5d4587bc7c4c5a8510a64f
Source dataset
uspto-grants-2015_07
Patent number
US09090671B2

Reaction notes

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