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Water → (+)-2-Octanol

HRID 1939757
Notes
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Reaction equation

HRID 1939757 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 13, 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 esters. The reaction mixture was treated in the same manner as in Example 13 to remove lipase, and the filtrate was subjected to simple distillation at 95° C. and 3 mmHg. 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 13
  • customto remove lipase
  • distillationthe filtrate was subjected to simple distillation at 95° C.
  • Sources & evidence

    ORD record
    ord-6f1669be0c324f058d3636f30cc8a859
    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