Water → 3-[1,3]Dioxolan-2-ylbenzyl alcohol

HRID 1198549Notes

Reaction equation

HRID 1198549 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9](OC)=[O:10].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[CH2:9][OH:10]

Participants

5

Reactant 3

HCID 962Water2×HCID 19102594Methyl 3-(1,3-dioxolan-2-yl)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 230829203-[1,3]Dioxolan-2-ylbenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 3-(1,3-dioxolan-2-yl)benzoate (11.0 g., 53 mmol) in tetrahydrofuran (50 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (3.2 g) in tetrahydrofuran (100 ml). The temperature rose to ca. 45° C. The mixture was stirred for a further 1 hour cooling to room temperature, then was cooled in ice whilst water (3.2 ml) 2M sodium hydroxide (6.4 ml) and more water (6.4 ml) were added dropwise. The mixture was filtered through a pad of Celite filter acid and the filtrate was evaporated to a colourless oil.

Workup

  1. customrose to ca. 45° C
  2. additionwere added dropwise
  3. filtrationThe mixture was filtered through a pad of Celite
  4. filtrationfilter acid
  5. customthe filtrate was evaporated to a colourless oil

Sources & evidence

ORD record
ord-65f85f1e9ef849c28e5137bc698ca974
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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