Sodium Hydroxide → (S)-1-Ethyl-2-oxocyclohexanepropanoic Acid

HRID 247648Notes

Reaction equation

HRID 247648 reaction equation
C[O:2][C:3](=[O:15])[CH2:4][CH2:5][C@:6]1([CH2:13][CH3:14])[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:12].[OH-].[Na+]>C(O)C>[CH2:13]([C@@:6]1([CH2:5][CH2:4][C:3]([OH:15])=[O:2])[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:12])[CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10375892(S)-1-Ethyl-2-oxocyclohexanepropanoic Acid Methyl Ester

Product 1

HCID 54536642(S)-1-Ethyl-2-oxocyclohexanepropanoic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (S)-1-ethyl-2-oxocyclohexanepropanoic acid methyl ester (3.25 mol, 689 g) in 1.4 L of ethanol was treated with 1.4 L of 2.5M sodium hydroxide. After 15 minutes at room temperature, the ethanol was removed on a rotary evaporator and the aqueous solution was extracted with ether (2×500 mL). It was acidified with 1 L of 6M hydrochloric acid and extracted with 1×1 L and 2×500 mL of ether. The extracts were combined, dried (magnesium sulfate) and concentrated to a yellow oil (605 g, 3.64 mol, 112%) which was used as in the next step.

Workup

  1. customthe ethanol was removed on a rotary evaporator
  2. extractionthe aqueous solution was extracted with ether (2×500 mL)
  3. extractionextracted with 1×1 L and 2×500 mL of ether
  4. dry with materialdried (magnesium sulfate)

Sources & evidence

ORD record
ord-7d6da17d80b245418bef8151d407a1f6
Source dataset
uspto-grants-1987_11
Patent number
US04709048

Reaction notes

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