Cesium carbonate → 2-(2-(2,2-Diethoxyethoxy)phenyl)ethanol

HRID 446487

Reaction equation

HRID 446487 reaction equation
Br[CH2:2][CH:3]([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6].C(=O)([O-])[O-].[Cs+].[Cs+].[OH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[OH:25]>CN(C=O)C>[CH2:5]([O:4][CH:3]([O:7][CH2:8][CH3:9])[CH2:2][O:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][CH2:17][OH:16])[CH3:6]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 822002-(2-Hydroxyethyl)phenol

Product 1

HCID 581685662-(2-(2,2-Diethoxyethoxy)phenyl)ethanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-bromo-1,1-diethoxyethane (5.13 g) was added to a stirred mixture of cesium carbonate (8.49 g) and 2-(2-hydroxyethyl)phenol (3.00 g) in DMF (20 mL). After 5 minutes the reaction mixture was heated at 80° C. 16 h, the reaction mixture was allowed to cool and partitioned between ethyl acetate and water. The ethyl acetate layer was washed with water (×3) then evaporated. Purification by silica gel chromatography eluting with ethyl acetate:iso-hexanes, 1:3 gave the subtitle compound as a green oil. Yield 3.6 g.

Workup

  1. custom16 h
  2. temperatureto cool
  3. custompartitioned between ethyl acetate and water
  4. washThe ethyl acetate layer was washed with water (×3)
  5. customthen evaporated
  6. customPurification by silica gel chromatography
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-379c8c3ccb1c41beac9c244098e88977
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Linked notes

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