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Water → 3-(4-Hydroxyphenyl)-7-methoxymethyloxy-3-methylchroman-4-one

HRID 1792393
Notes
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Reaction equation

HRID 1792393 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)([CH3:12])[CH2:8][O:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:23][O:24][CH2:25]Cl.O>CN(C)C=O>[OH:19][C:16]1[CH:17]=[CH:18][C:13]([C:7]2([CH3:12])[C:6](=[O:20])[C:5]3[C:10](=[CH:11][C:2]([O:1][CH2:23][O:24][CH3:25])=[CH:3][CH:4]=3)[O:9][CH2:8]2)=[CH:14][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 22033150HCID 22033150, compound

Product 1

HCID 220331393-(4-Hydroxyphenyl)-7-methoxymethyloxy-3-methylchroman-4-oneYield 66%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of 7-hydroxyl-3-(4-hydroxyphenyl)-3-methylchroman-4-one (4.65 g, 17.20 mmol) in dry dimethylformamide (120 ml) was added sodium hydride (454 mg, 18.92 mmol) at room tempetarure and stirred for 30 minutes. To the reaction mixture was then added methoxymethyl chloride (1.523 g, 18.92 mmol) at the same temperature and stirred for 2 h. When the reaction was completed, water was added to the reaction solution which was then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with column chromatography (n-hexane:ethyl acetate=8:2 to 7:3) to give 3.55 g (yield: 66%) of the title compound as a white solid.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with column chromatography (n-hexane:ethyl acetate=8:2 to 7:3)

Sources & evidence

ORD record
ord-550930fe43a0448fb9673af3bba9b2db
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07074819B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes