Potassium Phosphate, Tribasic → (R)-2-Chloro-1-(3-chlorophenyl)ethanol

HRID 576468Notes

Reaction equation

HRID 576468 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Mg+2].[Cl-].[Cl-].[Cl:12][CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=1)=[O:15].C1N=C(N)C2N=CN([C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H](N5C=C(C(N)=O)CC=C5)[C@H](O)[C@@H]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3O)C=2N=1>CC(C)CC(O)C.OCC(CO)O>[Cl:12][CH2:13][C@@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=1)[OH:15]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 168006Ethanone, 2-chloro-1-(3-chlorophenyl)-2×HCID 439153NadhHCID 5360315Magnesium Chloride

Product 1

HCID 10375278(R)-2-Chloro-1-(3-chlorophenyl)ethanol

Reagents, catalysts & solvents 2

HCID 753GlycerolSolventHCID 79104-Methyl-2-PentanolSolvent2×

Procedure

For the conversion, a mixture of 20 ml of a buffer (100 mM potassium phosphate, pH=8.5, 1 mM MgCl2, 10% glycerol), 20 g 2-chloro-1-(3-chlorophenyl)ethane-1-one dissolved in 80 ml 4-methyl-2-pentanol, 10 mg NAD and 20 000 U recombinant oxidoreductase from Pichia stipidis DSMZ 3651 was incubated at room temperature for 24 h with constant thorough mixing. After 24 h, more than 99% of the 2-chloro-1-(3-chlorophenyl)ethane-1-one used had been reduced. Subsequently, the 4-methyl-2-pentanol phase containing the product was separated from the aqueous phase, filtered, and the product (R)-2-chloro-1-(3-chlorophenyl)ethane-1-ol was obtained by distillation.

Workup

  1. waitAfter 24 h
  2. customwas separated from the aqueous phase
  3. filtrationfiltered

Sources & evidence

ORD record
ord-6e92961cf26148a594d91d4b1620891a
Source dataset
uspto-grants-2015_05
Patent number
US09040265B2

Reaction notes

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