Sodium Hydroxide → HCID 178445661, compound

HRID 1709152Notes

Reaction equation

HRID 1709152 reaction equation
[CH2:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([O:13]C)=[O:12])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>CO.O>[CH2:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 178445664HCID 178445664, compound

Product 1

HCID 178445661HCID 178445661, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 962WaterSolvent

Procedure

The cis methyl ester (14, 500 mg) was dissolved in methanol (5 ml) and stirred in a nitrogen atmosphere. A solution of NaOH in aqueous methanol (5 ml; 2.4 g NaOH in 30 ml water which was then diluted to 100 ml with methanol) was added and the mixture stirred for 24 hr at room temperature. The methanol was evaporated, water added, and then extracted with heptane (3×). The aqueous fraction was acidified to approximately pH 4 with dilute HCl, saturated with NaCl, and extracted with EtOAC (3×). The EtOAC extract was washed with water and dried over Na2O4, then evaporated in vacuo to give the cis-carboxylic acid (9, 0.35 g). A small aliquot was esterfied with diazomethane and analyzed by HPLC. Less than 1% of the trans isomer was present. The reaction was repeated on the remaining 400 mg. A total of 626 mg of the cis acid was obtained.

Workup

  1. additionwas added
  2. stirringthe mixture stirred for 24 hr at room temperature
  3. customThe methanol was evaporated
  4. additionwater added
  5. extractionextracted with heptane (3×)
  6. extractionextracted with EtOAC (3×)
  7. extractionThe EtOAC extract
  8. washwas washed with water
  9. customdried over Na2O4
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-1cbb6674370d4ef888da40a21972ceaa
Source dataset
uspto-grants-1990_08
Patent number
US04948790

Reaction notes

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