3-Hydroxybenzyl alcohol → [3-(2-Methoxyethoxy)phenyl]methanol

HRID 1685124Notes

Reaction equation

HRID 1685124 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[OH-].[Na+].Br[CH2:13][CH2:14][O:15][CH3:16]>C(O)C.O>[CH3:16][O:15][CH2:14][CH2:13][O:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 14798Sodium HydroxideHCID 809722-Bromoethyl methyl ether

Product 1

HCID 20110194[3-(2-Methoxyethoxy)phenyl]methanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-hydroxybenzyl alcohol (27A) (12.41 g, 100 mmol) in ethanol (150 mL) was added aqueous NaOH (10 N, 10 mL), followed by 1-bromo-2-methoxyethane (27B) (13.9 g). The reaction mixture was heated to reflux overnight. Then the reaction mixture was allowed to cool to RT, and diluted with water. The mixture was subsequently extracted with CH2Cl2, and the combined organic phase was dried with anhydrous MgSO4 filtered, and concentrated in vacuum to give the product (27C) a yellow oil, which was used for the next reaction without further purification. 1H NMR (300 MHz, CDCl3): δ 1.82 (br, 1H), 3.44 (s, 3H), 3.74 (t, 2H, J=4.8 Hz), 4.12 (t, 2H, J=4.8 Hz), 4.65 (s, 2H), 6.84-6.95 (m, 3H), 7.22-7.26 (m, 1H). LCMS: purity >94%. ESI-MS: M/Z 183(M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. extractionThe mixture was subsequently extracted with CH2Cl2
  4. dry with materialthe combined organic phase was dried with anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-0f6e49f8da1346d39829c03b6c13e69c
Source dataset
uspto-grants-2012_04
Patent number
US08148367B2

Reaction notes

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