2-Methoxycarbonyl-heptadecanedioic acid 1-methyl ester → Heptadecanedioic acid

HRID 444980Notes

Reaction equation

HRID 444980 reaction equation
C[O:2][C:3](=[O:26])[CH:4](C(OC)=O)[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][CH2:18][C:19]([OH:21])=[O:20]>[OH-].[K+]>[C:19]([OH:21])(=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:26])=[O:2]

Participants

3

Reactant 1

HCID 866192452-Methoxycarbonyl-heptadecanedioic acid 1-methyl ester

Product 1

HCID 3083765Heptadecanedioic acid

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
140 °C

Procedure

2-Methoxycarbonyl-heptadecanedioic acid 1-methyl ester (4.63, 12.4 mmol g) was dissolved in 20% aqueous KOH (15 ml) by heating. The resulting solution was refluxed for 2.5 h. The cold reaction mixture was carefully concentrated. The residue was suspended in water (30 ml) on an ice bath and acidified with 10% aqueous HCI. The resulting slurry was refluxed for 2 h. After cooling the precipitate was isolated by filtration and dried over night in vacuo. The compound was decarboxylated by heating under stirring at 140° C. for 2 h. (the reaction should be followed, heating to 180° might be necessary). The crude product (4.0 g, 100%) was used without further purification. HPLC-MS: 323 (M+Na), R14.61. 1H-NMR (DMSO-d6): δ 1.22 (br s, 22H) 1.47 (m, 4H), 2.18 (t, 4H).

Workup

  1. temperatureby heating
  2. temperatureThe resulting solution was refluxed for 2.5 h
  3. customThe cold reaction mixture
  4. concentrationwas carefully concentrated
  5. customThe residue was suspended in water (30 ml) on an ice bath
  6. temperatureThe resulting slurry was refluxed for 2 h
  7. temperatureAfter cooling the precipitate
  8. customwas isolated by filtration
  9. customdried over night in vacuo
  10. temperatureby heating
  11. customthe reaction
  12. temperatureheating to 180°
  13. customThe crude product (4.0 g, 100%) was used without further purification

Sources & evidence

ORD record
ord-3bc330df76fc4cd4bd1a060fc789cff8
Source dataset
uspto-grants-2013_07
Patent number
US08476228B2

Reaction notes

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