Monobenzone → HCID 21830637, compound

HRID 1600972Notes

Reaction equation

HRID 1600972 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:17][CH:18]([OH:27])[CH2:19][CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1.[OH-].[Na+]>C(O)C.O>[C:2]1([CH2:1][O:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:17][CH:18]([OH:27])[CH2:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:13][CH:14]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7638MonobenzoneHCID 14798Sodium HydroxideHCID 22465338HCID 22465338, compound

Product 1

HCID 21830637HCID 21830637, compoundYield 61.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Prepared according to the method described in Example 24b) from 4-(benzyloxy)phenol (1.00 g), (±)-α-(chloromethyl)-3-pyridinepropanol (0.50 g) and sodium hydroxide (0.23 g) in ethanol (20 ml) and water (5 ml) with heating at reflux for 45 minutes. After work up the residue was purified by column chromatography over silica eluting with dichloromethane:ethanol (19:1) and then using a fresh column of silica eluting with ethyl acetate to give the title compound as a solid (0.58 g). Recrystallisation from ethyl acetate:hexane gave colourless crystals.

Workup

  1. customPrepared
  2. temperaturewith heating
  3. temperatureat reflux for 45 minutes
  4. customAfter work up the residue was purified by column chromatography over silica eluting with dichloromethane:ethanol (19:1)

Sources & evidence

ORD record
ord-30a0e2e31be0464fb0f27e52969d71f3
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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