HCID 11564557, compound → HCID 58249836, compound

HRID 1513539Notes

Reaction equation

HRID 1513539 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][C:5](=[O:10])[CH2:6][CH2:7][CH2:8][Cl:9].[H][H]>CO>[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH:5]([OH:10])[CH2:6][CH2:7][CH2:8][Cl:9]

Participants

4

Reactant 2

HCID 11564557HCID 11564557, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58249836HCID 58249836, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 214.9 g portion of the above-mentioned crude 6-chloro-3-oxo-hexanoic acid methyl ester (1), Ru2Cl4-[(S)-Segphos]2(NEt)3 (60.7 mg, 0.0725×10−3 mol) and methanol (130 ml) were put into a 500 ml capacity autoclave and stirred with hydrogen (3 MPa) at 65 to 70° C. for 6 hours. After completion of the reaction, the solvent was evaporated under a reduced pressure using an evaporator, and then the residue was distilled under a reduced pressure (75 to 85° C./0.1 ton) to obtain 6-chloro-3-hydroxy-hexanoic acid methyl ester (2); 178.2 g {GC purity; 80.1%, pure amount; 142.7 g (0.790 mol, yield 44%/4-chlorobutanoic acid chloride)}.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated under a reduced pressure
  3. customan evaporator
  4. distillationthe residue was distilled under a reduced pressure (75 to 85° C./0.1 ton)

Sources & evidence

ORD record
ord-7bd490fa9d134ed59a64309fbd876f3b
Source dataset
uspto-grants-2012_07
Patent number
US08217192B2

Reaction notes

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