Water → 2-[Bis(4-methoxymethoxyphenyl)methyl]benzyl alcohol

HRID 36450Notes

Reaction equation

HRID 36450 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][O:32][CH3:33])=[CH:26][CH:25]=2)[C:12]2[CH:23]=[CH:22][CH:21]=[CH:20][C:13]=2[C:14](OCOC)=[O:15])=[CH:7][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:33][O:32][CH2:31][O:30][C:27]1[CH:26]=[CH:25][C:24]([CH:11]([C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:10][CH:9]=2)[C:12]2[CH:23]=[CH:22][CH:21]=[CH:20][C:13]=2[CH2:14][OH:15])=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19938166Methoxymethyl 2-[bis(4-methoxymethoxyphenyl)methyl]benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 539143042-[Bis(4-methoxymethoxyphenyl)methyl]benzyl alcoholYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 500 ml of tetrahydrofuran was dissolved 74 g of methoxymethyl 2-[bis(4-methoxymethoxyphenyl)methyl]-benzoate obtained by Reference Example 3. The solution was ice-cooled, 10 g of lithium aluminum hydride was added thereto, and the mixture was stirred for 10 minutes. The reaction mixture was stirred for additional 30 minutes at room temperature, and ice cooled, and then 10 ml of water, 10 ml of aqueous 15% sodium hydroxide and 30 ml of water were added thereto in order. The mixture was filtered by use of a filter aid and then concentrated under reduced pressure to afford 53.54 g of the desired compound as an oily matter.

Workup

  1. customobtained by Reference Example 3
  2. temperaturecooled
  3. stirringThe reaction mixture was stirred for additional 30 minutes at room temperature
  4. temperatureice cooled
  5. filtrationThe mixture was filtered by use of a filter aid
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b5a651aec1114e6c87a53893f6500034
Source dataset
uspto-grants-1995_05
Patent number
US05413997

Reaction notes

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