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Water → (+)-2-Octanol

HRID 1939751
Notes
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Reaction equation

HRID 1939751 reaction equation
[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]CCCC(OC)=O)(OC)=O.[OH2:19]>>[CH3:1][C@H:5]([OH:19])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 962WaterHCID 74415Dimethyl dodecanedioate

Product 1

HCID 2723888(+)-2-Octanol

Procedure

Interesterification was carried out in the same manner as in Example 9, except for replacing dimethyl tetradecadicarboxylate with 140 g of dimethyl decamethylenedicarboxylate at 80° C. for 25 hours. The water content of the reaction system was 0.04% by weight, and 95% of the lipase particles had a particle size of 20 to 60 μm. Gas chromatography of the reaction mixture revealed that 58 mol % of (R,S)-2-octanol had been converted to its decamethylenedicarboxylic acid ester. The reaction mixture was treated in the same manner as in Example 9 to remove lipase, and the filtrate was subjected to simple distillation at 95° C. and 3 mmHg. However, it was impossible to isolate (S)-(-)-2-octanol with high purity due to co-distillation of other components.

Workup

  1. customat 80° C.
  2. customfor 25 hours
  3. additionThe reaction mixture was treated in the same manner as in Example 9
  • customto remove lipase
  • distillationthe filtrate was subjected to simple distillation at 95° C.
  • Sources & evidence

    ORD record
    ord-4c0d3db646b34dc5b0ff1578e60e58ad
    Source dataset
    uspto-grants-1997_12
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US05696299

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes