(2R)-2-methoxypropanoic acid → 2-Methoxy-1-propanol, (2S)-

HRID 2740Notes

Reaction equation

HRID 2740 reaction equation
[CH3:1][O:2][C@H:3]([CH3:7])[C:4]([OH:6])=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].CO[C@H](C)CO>>[CH3:1][O:2][C@@H:3]([CH3:7])[CH2:4][OH:5].[CH3:1][O:2][C@@H:3]([CH3:7])[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 2733584(2R)-2-methoxypropanoic acidHCID 27335882-Methoxy-1-propanol, (2R)-HCID 21226445Aluminium lithium hydride

Product 2

HCID 6424022-Methoxy-1-propanol, (2S)-HCID 57025662-methoxypropanoic acid, (S)-

Procedure

By reduction of the (+)-(R)-2-methoxy-propionic acid known from the prior art with lithium aluminium hydride (LiAlH4) the (-)-(R)-2-methoxy-propanol is obtained with a boiling point of 70° C. under a pressure of 76 mbar and a specific rotation of [α]D25 =-15.8° (c=100). The corresponding (+)-(S)-2-methoxy-propanol with a boiling point of 70° C. under a pressure of 76 mbar and a rotation of [α]D25 =+16.5° (c=100) is obtained analogously from the equally well known (-)-(S)-2-methoxy-propionic acid.

Workup

  1. customis obtained with a boiling point of 70° C. under a pressure of 76 mbar
  2. customa specific rotation of [α]D25 =-15.8° (c=100)

Sources & evidence

ORD record
ord-5f18c5914e004a9f8905dfa1893ebe5b
Source dataset
uspto-grants-1998_03
Patent number
US05731318

Reaction notes

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