4-Hydroxybenzyl Alcohol → [4-(2,2-Diethoxy-ethoxy)-phenyl]-methanol

HRID 470951Notes

Reaction equation

HRID 470951 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.Br[CH2:17][CH:18]([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21].O>CN(C=O)C>[CH2:20]([O:19][CH:18]([O:22][CH2:23][CH3:24])[CH2:17][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][OH:7])=[CH:10][CH:11]=1)[CH3:21]

Participants

6

Reactant 4

HCID 1254-Hydroxybenzyl AlcoholHCID 962WaterHCID 10796Cesium carbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 57989210[4-(2,2-Diethoxy-ethoxy)-phenyl]-methanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Caesium carbonate (39.4 g) was added to a solution of 4-hydroxymethyl-phenol (10 g) and 2-bromo-1,1-diethoxyethane (12.73 mL) in DMF (200 mL) and the resulting mixture stirred at 90° C. for 16 h. The reaction was poured into water (500 mL) and extracted with ethyl acetate (3×250 mL). The combined organic solutions were washed with water (250 mL) and brine (250 mL), then dried over sodium sulphate, filtered and evaporated in vacuo. Purification was by silica gel chromatography eluting with an isohexane to diethyl ether gradient to give the subtitled compound as a yellow oil. Yield 9.5 g.

Workup

  1. extractionextracted with ethyl acetate (3×250 mL)
  2. washThe combined organic solutions were washed with water (250 mL) and brine (250 mL)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification
  7. washeluting with an isohexane to diethyl ether gradient

Sources & evidence

ORD record
ord-95e384746b78438783d4c655c17300d0
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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