Methane → HCID 12799989, compound

HRID 2412628Notes

Reaction equation

HRID 2412628 reaction equation
[CH2:1]([CH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:28]([O:30]C)=[O:29])[CH:26]=2)[NH:21][CH2:20]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH-].[K+].C>C(O)C.O>[CH2:1]([CH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:28]([OH:30])=[O:29])[CH:26]=2)[NH:21][CH2:20]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 297MethaneHCID 14797Potassium HydroxideHCID 12799980HCID 12799980, compound

Product 1

HCID 12799989HCID 12799989, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

(RS)-Methyl 3-(n-octadecyl)indoline-5-carboxylate (13.6 g) in ethanol (380 ml), containing potassium hydroxide (2.7 g) and water (50 ml), was refluxed with stirring for 24 hours. The solvent was removed in vacuo to give an off-white solid. The solid was dissolved in water, and the solution treated with charcoal and filtered through diatomaceous earth. Glacial acetic acid (50 ml) was slowly added to the stirred solution and an off-white solid was collected, which was recrystallised from ethyl acetate to give (RS)-3-(n-octadecyl)indoline-5-carboxylic acid (9.1 g), in the form of a white solid, m.p. 84°-87° C.

Workup

  1. temperaturewas refluxed
  2. customThe solvent was removed in vacuo
  3. customto give an off-white solid
  4. filtrationfiltered through diatomaceous earth
  5. additionGlacial acetic acid (50 ml) was slowly added to the stirred solution
  6. customan off-white solid was collected
  7. customwhich was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-6c150fefabb14d7d9edad5bb195f1859
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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