Acetic Acid → HCID 18429138, compound

HRID 1280174Notes

Reaction equation

HRID 1280174 reaction equation
[C:1]([O:4][CH:5]([CH2:16][CH2:17][CH2:18][Cl:19])[C:6]([O:8]CC1C=CC=CC=1)=[O:7])(=[O:3])[CH3:2].C(O)(=O)C>C(OCC)(=O)C.[Pd]>[C:1]([O:4][CH:5]([CH2:16][CH2:17][CH2:18][Cl:19])[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 18429349HCID 18429349, compound

Product 1

HCID 18429138HCID 18429138, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl 2-acetoxy-5-chloropentanoate (52.6 g, 0.19 mol) was dissolved in ethyl acetate (350 ml) and acetic acid (25 ml) and hydrogenated at 10 psi in a Parr apparatus in the presence of a Pd/C catalyst (5%, 2.5 g). After completion, the catalyst was filtered off and the volatiles were evaporated. The residue was dried in vacuo ( 1 mm Hg, 100° C.), and 35 g (98%) of the crude product was isolated and used without further purification.

Workup

  1. filtrationAfter completion, the catalyst was filtered off
  2. customthe volatiles were evaporated
  3. customThe residue was dried in vacuo ( 1 mm Hg, 100° C.)

Sources & evidence

ORD record
ord-9fd168f830ff49f4839388fa9627f2a1
Source dataset
uspto-grants-2002_09
Patent number
US06448442B1

Reaction notes

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