Ethyl Acetate → HCID 66822316, compound

HRID 445393Notes

Reaction equation

HRID 445393 reaction equation
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3](=N)[O-:4].[C:18](OCC)(=[O:20])C>O>[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]([O:20][CH3:18])=[O:4]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 86663642HCID 86663642, compound

Product 1

HCID 66822316HCID 66822316, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A two-phase solution of the 2-hydroxy-8-phenyloctanimidate, ethyl acetate (50 mL), and water (50 mL) was stirred overnight. The layers were separated and the organic phase was dried (Na2SO4), filtered and concentrated to yield methyl 2-hydroxy-8-phenyloctanoate as an oil. The oil was dissolved in 9:1 dioxane-water (50 mL) containing LiOH (1.7 g). After 2 h of stirring, the mixture was acidified with 2N HCL to pH˜3. The resulting mixture was extracted twice with EtOAc and the combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated to yield 2-hydroxy-8-phenyloctanoic acid as a solid.

Workup

  1. customThe layers were separated
  2. dry with materialthe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3e8a699a197246f88fa517852016733a
Source dataset
uspto-grants-2013_07
Patent number
US08476302B2

Reaction notes

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