Ethanol → 7-[Acetyl(4-hydroxynonyl)amino]heptanoic acid

HRID 1288344Notes

Reaction equation

HRID 1288344 reaction equation
O1CCCCC1[O:7][CH:8]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:9][CH2:10][CH2:11][N:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24]CC)=[O:23])[C:13](=[O:15])[CH3:14].C(O)C.[OH-].[Na+]>Cl.O>[OH:7][CH:8]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:9][CH2:10][CH2:11][N:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])[C:13](=[O:15])[CH3:14]

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 21503952HCID 21503952, compound

Product 1

HCID 215039297-[Acetyl(4-hydroxynonyl)amino]heptanoic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Procedure

A solution is prepared from ethyl 7-{N-[4-(2-tetrahydropyranyloxy)nonyl]acetamido}heptanoate (4.5 g., 0.01 mole), ethanol (50 ml.) and 4 drops of concentrated hydrochloric acid, and kept at ambient temperature for 4.5 hours. Then to the reaction mixture is added a solution of sodium hydroxide (0.72 g., 0.018 mole) in water (8 ml.) and the mixture is kept at ambient temperature for an additional twenty hours. Most of the ethanol is removed by evaportion in vacuo and the resulting solution is diluted with water (100 ml.). This solution is extracted, once with ether, then acidified with hydrochloric acid. The oil that separates is extracted into ether, the ethereal extract is dried over sodium sulfate, then the solvent is removed under vacuum to give 7-[N-(4-hydroxynonyl)acetamido]heptanoic acid as a yellow oil; pmr (CDCl3) δ 0.93 (3H,m CH3), 2.10 (3H,s CH3CO), 3.38 (4H,m NCH), 7.03 (2H,s COOH, OH).

Workup

  1. waitthe mixture is kept at ambient temperature for an additional twenty hours
  2. customMost of the ethanol is removed by evaportion in vacuo
  3. additionthe resulting solution is diluted with water (100 ml.)
  4. extractionThis solution is extracted, once with ether
  5. extractionThe oil that separates is extracted into ether
  6. extractionthe ethereal extract
  7. dry with materialis dried over sodium sulfate
  8. customthe solvent is removed under vacuum

Sources & evidence

ORD record
ord-5f506f6bde5c49ffaba41689b4f6b142
Source dataset
uspto-grants-1976_10
Patent number
US03987091

Reaction notes

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