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Sodium sulfate decahydrate → 2-[3,5-Bis(methoxymethoxy)phenyl]ethanol

HRID 499861
Notes
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Reaction equation

HRID 499861 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]([CH2:21][C:22](OC)=[O:23])[CH:14]=[C:15]([O:17][CH2:18][O:19][CH3:20])[CH:16]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:7][O:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]([CH2:21][CH2:22][OH:23])[CH:14]=[C:15]([O:17][CH2:18][O:19][CH3:20])[CH:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 23116398Methyl 3,5-bis(methoxymethoxy)phenylacetate

Product 1

HCID 231163592-[3,5-Bis(methoxymethoxy)phenyl]ethanolYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
4 °C

Procedure

A solution of lithium aluminum hydride (1.0 g, 26 mmol) in tetrahydrofuran (50 mL) was cooled to 4° C., and a solution of methyl 3,5-bis(methoxymethoxy)phenylacetate (5.3 g, 20 mmol) obtained in Example 1, Step 1 in tetrahydrofuran (50 mL) was added dropwise thereto, followed by stirring at 4° C. for 30 minutes. To the reaction mixture was added anhydrous sodium sulfate decahydrate to stop the reaction, and the mixture was stirred at room temperature for 12 hours. The resulting suspension was filtered under reduced pressure, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-1/1) to obtain 2-[3,5-bis(methoxymethoxy)phenyl]ethanol (4.6 g, 98%).

Workup

  1. customthe reaction
  2. stirringthe mixture was stirred at room temperature for 12 hours
  3. filtrationThe resulting suspension was filtered under reduced pressure
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-1/1)

Sources & evidence

ORD record
ord-6d225c30d1ae44e39d28c5e58dbe5ee0
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07767693B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes