Citric Acid → (3R)-3-Hydroxydecanoic acid

HRID 1591057Notes

Reaction equation

HRID 1591057 reaction equation
O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.P([O-])(O)(O)=O.[K+].S([O-])([O-])(=O)=O.[Mg+2].[O:25]=[C:26]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:27][C:28]([O-:30])=[O:29].[K+].[OH-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[OH:25][C@H:26]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:27][C:28]([OH:30])=[O:29]

Participants

8

Reactant 6

HCID 311Citric AcidHCID 14797Potassium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 516951Monobasic potassium phosphateHCID 23669112HCID 23669112, compound

Product 1

HCID 5312798(3R)-3-Hydroxydecanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Baker's yeast (Saccharomyces cerevisiae, Malteserkors®, De danske Spritfabrikker, 640 g), D-glucose (720 g), potassium dihydrogenphosphate (1.6 g) and magnesium sulfate (0.8 g) in water (2 l) were stirred at room temperature for 30 minutes. A solution of the above potassium 3-oxodecanoate in water (1.5 l) was added. The mixture was stirred at ambient temperature and pH was kept between 6.0 and 6.5 by automatic titration with 1M potassium hydroxide or 1M citric acid. After 48 hours Celite® was added, and after stirring for 30 minutes more the mixture was filtered. The filtrate was acidified to pH 2.5 with concentrated hydrochloric acid, extracted with methylene chloride (2×2 l), dried and evaporated in vacuo to give crude 3(R)-hydroxydecanoic acid.

Workup

  1. additionAfter 48 hours Celite® was added
  2. stirringafter stirring for 30 minutes more the mixture
  3. filtrationwas filtered
  4. extractionextracted with methylene chloride (2×2 l)
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-573eabb17d104176b0185eb09f2be8b3
Source dataset
uspto-grants-1993_04
Patent number
US05206229

Reaction notes

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