Hydrochloric Acid → HCID 25010499, compound

HRID 1925675Notes

Reaction equation

HRID 1925675 reaction equation
[CH2:1](/[C:3](=[CH:9]\[CH:10]=[CH:11]\[CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19]/[CH:20]=[CH:21]\[CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH3:26])/[C:4]([O:6]CC)=[O:5])[CH3:2].[Li+].[OH-].Cl>C(O)C.O>[CH2:1](/[C:3](=[CH:9]\[CH:10]=[CH:11]\[CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19]/[CH:20]=[CH:21]\[CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH3:26])/[C:4]([OH:6])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 25010670HCID 25010670, compound

Product 1

HCID 25010499HCID 25010499, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Procedure

Ethyl-(2E,4E,8Z,11Z,14Z,17Z)-2-ethyl-eicosa-2,4,8,11,14,17-hexaneoate (17) (0.040 g, 0.112 mmol) was dissolved in ethanol (4 mL) and added a solution of LiOH×H2O (0.038 g, 0.898 mmol) in water (1 mL). The mixture was stirred at ambient temperature for 15 hours, followed by five hours at 70° C. The mixture was cooled, added 1M HCl until pH=1 and diluted with water (2 mL). The mixture was extracted twice with heptane (10 mL) and the combined organic extracts were dried (Na2SO4). Purification by flash chromatography (heptane:EtOAc 95:5 then 4:1) afforded 0.028 g (76%) of the title compound as a pale yellow oil. 1H-NMR (200 MHz, CDCl3): δ 0.90-1.07 (2×t, 6H), 2.00-2.10 (m, 2H), 2.20-2.30 (m, 4H), 2.35-2.50 (q, 2H), 2.75-2.90 (m, 6H), 5.27-5.44 (m, 8H), 6.05-6.20 (m, 1H), 6.30-6.43 (m, 1H), 7.50-7.70 (m, 1H); MS (electrospray): 327.2 [M−H]−.

Workup

  1. waitfollowed by five hours at 70° C
  2. temperatureThe mixture was cooled
  3. extractionThe mixture was extracted twice with heptane (10 mL)
  4. dry with materialthe combined organic extracts were dried (Na2SO4)
  5. customPurification by flash chromatography (heptane:EtOAc 95:5

Sources & evidence

ORD record
ord-82a64fb60f5c42f6aab7795a53741e5c
Source dataset
uspto-grants-2012_05
Patent number
US08178708B2

Reaction notes

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