tert-Butanol → beta-Methylenephenethyl alcohol

HRID 17783

Reaction equation

HRID 17783 reaction equation
CC[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:11]([OH:15])(C)(C)C.[Se](=O)=O.C1(C(C)=C)C=CC=CC=1>C(Cl)Cl.C(O)(=O)C>[OH:15][CH2:11][C:9]([C:8]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[CH2:10]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 7407Alpha-MethylstyreneHCID 15600DecaneHCID 24007Selenium Dioxide

Product 1

HCID 80106beta-Methylenephenethyl alcoholYield 59%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A 12.5 ml of decane solution of 5 to 6 mol/L of per-tert-butylalcohol is diluted with 50 ml of methylene chloride, then 111 mg of selenium dioxide and 90.1 mg of an acetic acid were added thereto to react while stirring at room temperature for 30 min. Then, 6.5 ml of 2-phenylpropene was added to the reaction solution to react while stirring for 72 hours, followed by condensation under reduced pressure, and purification by silica gel column chromatography to obtain 3.98 g of 3-hydroxy-2-phenylpropene (yield: 59%). Measurement results by 1H-NMR and 13C-NMR of 3-hydroxy-2-phenylpropene obtained are shown below.

Workup

  1. customto react
  2. customto react
  3. stirringwhile stirring for 72 hours
  4. customfollowed by condensation under reduced pressure, and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-19597bdefb3548119f1a52e9b0ae7935
Source dataset
uspto-grants-2010_06
Patent number
US07741242B2

Linked notes

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