Salicyl Alcohol → [2-(2-Morpholinoethoxy)phenyl]methanol

HRID 1359664

Reaction equation

HRID 1359664 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].Cl.Cl[CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>[OH-].[Na+]>[N:14]1([CH2:13][CH2:12][O:1][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH2:4][OH:5])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 5146Salicyl AlcoholHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 7164615[2-(2-Morpholinoethoxy)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2-hydroxybenzyl alcohol (1.295 g, 10.4 mmol) and 4-(2-chloroethyl)morpholine hydrochloride (1.94 g, 10.4 mmol) in 2N NaOH (10.5 mL) was stirred at rt for 14 hours. The precipitate was collected by vacuum filtration, washed with 1N NaOH, redissolved in DCM and washed with 1N NaOH. The aqueous layer was extracted with more DCM (2×). The combined DCM was dried and concentrated to give [2-(2-morpholin-4-yl-ethoxy)-phenyl]-methanol which was used without further purification.

Workup

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washwashed with 1N NaOH
  3. dissolutionredissolved in DCM
  4. washwashed with 1N NaOH
  5. extractionThe aqueous layer was extracted with more DCM (2×)
  6. dry with materialThe combined DCM was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7b584bb1f44649918b9acb5561442590
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Linked notes

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