Sodium Hydroxide → (2E)-2-Propyl-2-pentenoic acid

HRID 1089589Notes

Reaction equation

HRID 1089589 reaction equation
C([O:3][C:4](=[O:12])[C:5]([CH2:9][CH2:10][CH3:11])=[CH:6][CH2:7][CH3:8])C.[OH-].[Na+].C(C(=CCC)C(O)=O)CC.C(C(C=CC)C(O)=O)CC>CO>[CH2:9](/[C:5](=[CH:6]\[CH2:7][CH3:8])/[C:4]([OH:12])=[O:3])[CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 1048932-Propyl-2-pentenoic acidHCID 1353102-Propyl-3-pentenoic acidHCID 54033083HCID 54033083, compound

Product 1

HCID 6437068(2E)-2-Propyl-2-pentenoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

10 g of 2-propyl-2-pentenoic acid ethyl ester according to Example 1 are added to a solution of 20 g of sodium hydroxide in 150 ml of methanol and left stand at room temperature. After 5 days and accompanied by the recovery of the methanol, the mixture is worked up in conventional manner following acidification. A mixture of 2-propyl-2-pentenoic acid (E-isomer) and 2-propyl-3-pentenoic acid (E-isomer) in a ratio of approximately 80:20 is obtained in an almost quantitative yield, which is separated by precision distillation on an effective column and gives E-2-propyl-2-pentenoic acid with b.p.15 135° to 136° C.

Workup

  1. waitleft stand at room temperature
  2. customis obtained in an almost quantitative yield, which
  3. customis separated by precision distillation on an effective column

Sources & evidence

ORD record
ord-bda768c25e5144c5b1e3b16ad641bfe5
Source dataset
uspto-grants-1990_10
Patent number
US04966996

Reaction notes

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