Water → 2-Methylpentane

HRID 446374Notes

Reaction equation

HRID 446374 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.Br[CH2:18][CH:19]([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22].O>CN(C=O)C>[CH3:13][CH2:12][CH2:11][CH:10]([CH3:15])[CH3:9].[CH2:21]([O:20][CH:19]([O:23][CH2:24][CH3:25])[CH2:18][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][OH:7])=[CH:11][CH:12]=1)[CH3:22]

Participants

7

Reactant 4

HCID 962WaterHCID 10393TyrosolHCID 10796Cesium carbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 2

HCID 78922-MethylpentaneHCID 579889402-(4-(2,2-Diethoxyethoxy)phenyl)ethanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Cesium carbonate (28.3 g) was added to a solution of 4-(2-hydroxyethyl)phenol (10 g) and 2-bromo-1,1-diethoxyethane (11.8 mL) in DMF (150 mL). The resulting suspension was heated at 90° C. for 16 h. The reaction was poured into water (500 mL). The aqueous phase was extracted with ethyl acetate (3×200 mL). The combined organic solutions were washed with water (200 mL) and brine (200 mL), then dried over magnesium sulfate, filtered and evaporated in vacuo. Purification was by silica gel chromatography eluting with isohexane to 1:1 ethyl acetate:isohexane gradient to give the subtitled compound as a yellow oil. Yield 10 g.

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate (3×200 mL)
  2. washThe combined organic solutions were washed with water (200 mL) and brine (200 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification
  7. washeluting with isohexane to 1:1 ethyl acetate

Sources & evidence

ORD record
ord-3fd374b80f66426dbb5facfed8677a38
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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