3-Hydroxybenzyl alcohol → HCID 55248013, compound

HRID 471054Notes

Reaction equation

HRID 471054 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][CH2:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1.Br[CH2:17][CH:18]([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]>CN(C=O)C>[CH2:20]([O:19][CH:18]([O:22][CH2:23][CH3:24])[CH2:17][O:15][C:11]1[CH:10]=[C:9]([CH2:8][OH:7])[CH:14]=[CH:13][CH:12]=1)[CH3:21]

Participants

5

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 10796Cesium carbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 55248013HCID 55248013, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (7.87 g) was added to a solution of 3-(hydroxymethyl)phenol (2.5 g) and 2-bromo-1,1-diethoxyethane (3.97 g) in DMF (40 mL) and the resultant mixture was heated at 90° C. for 18 hours. The mixture was cooled to room temperature and partitioned between ethyl acetate and brine, the organic layer was washed twice with brine, dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography using 30% ethyl acetate in isohexane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 1.9 g.

Workup

  1. custompartitioned between ethyl acetate and brine
  2. washthe organic layer was washed twice with brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customThe crude product was purified by flash silica chromatography
  7. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-bb8d96b40de145afb17f57dae1468453
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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