Hydrochloric Acid → HCID 11288385, compound

HRID 1781971Notes

Reaction equation

HRID 1781971 reaction equation
[CH2:1]1[CH2:20][O:19][C:3]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])([CH2:4][C:5]([O:7]CC)=[O:6])[O:2]1.O[Li].O.C1COCC1.Cl>O>[CH2:20]1[CH2:1][O:2][C:3]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])([CH2:4][C:5]([OH:7])=[O:6])[O:19]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 59537271HCID 59537271, compound

Product 1

HCID 11288385HCID 11288385, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 25 mL flask were added ethyl 3,3-ethylenedioxydodecanoate (1.131 g, 3.95 mmol), LiOH.H2O (840 mg, 20 mmol), THF (5 mL), and water (5 mL). The mixture was stirred at room temperature overnight. The solution was acidified by the addition of 1 M HCl (50 mL), and extracted with ethyl acetate (3×50 mL). The organic layers were combined and washed once with brine. The organic phase was dried (MgSO4) and concentrated to give 3,3-ethylenedioxydodecanoic acid (0.824 g, 3.19 mmol) in 81% yield. 1H NMR (500 MHz, CDCl3) δ 0.88 (t, J=7 Hz, 3H), 1.20-1.44 (m, 14H), 1.72-1.80 (m, 2H), 2.72 (s, 2H), 3.98-4.10 (m, 4H); 13C NMR (125 MHz, CDCl3) δ 13.9, 22.5, 23.3, 29.13, 29.35, 29.39, 29.50, 31.7, 37.5, 42.2, 64.9 (2 C), 109.2, 174.8.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washwashed once with brine
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-082ac3331501484a9c124c4ecaa3c4fc
Source dataset
uspto-grants-2009_03
Patent number
US07498292B2

Reaction notes

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