DL-2-Phenoxypropionic acid → 2-Phenoxy-1-propanol

HRID 2051915Notes

Reaction equation

HRID 2051915 reaction equation
[BH4-].[O:2]([CH:9]([CH3:13])[C:10](O)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCCC1>[O:2]([CH:9]([CH3:13])[CH2:10][OH:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 13658DL-2-Phenoxypropionic acidHCID 28123Borohydride

Product 1

HCID 201292-Phenoxy-1-propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 200 ml of one molar borohydride in tetrahydrofuran chilled in an ice bath under nitrogen is added dropwise with stirring 24.9 g of 2-phenoxypropionic acid in 100 ml of dry tetrahydrofuran over 25 minutes. The mixture is allowed to stand at room temperature for 23 hours and is poured onto ice. After standing, the mixture is extracted with dichloromethane and the extracts dried (magnesium sulfate) and concentrated under vacuum to give the product as a yellow oil.

Workup

  1. additionis added dropwise
  2. additionis poured onto ice
  3. extractionthe mixture is extracted with dichloromethane
  4. dry with materialthe extracts dried (magnesium sulfate)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-841c7e7d96ea4d729f7885083cea3edf
Source dataset
uspto-grants-1980_01
Patent number
US04182776

Reaction notes

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