Hydrochloric Acid → HCID 86641234, compound

HRID 1958750Notes

Reaction equation

HRID 1958750 reaction equation
C[O:2][CH:3](OC)[CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:10]=1.Cl>C1COCC1.O>[CH2:16]([O:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[O:2])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68744497HCID 68744497, compound

Product 1

HCID 86641234HCID 86641234, compoundYield 107.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 1-(5,5-dimethoxypentyloxy)-3-(hexyloxy)benzene (127 mg, 0.39 mmol) and 2 M aq HCl (0.47 mL, 0.94 mmol) in THF (4.5 mL), H2O (0.28 mL) was stirred at rt overnight. Later, the reaction was heated at 50° C. for 5 h. After cooling to rt the reaction mixture was diluted with H2O, extracted with Et2O (3×), washed (aq NaHCO3, brine), dried (Na2SO4) and concentrated under reduced pressure to yield 5-(3-(hexyloxy)phenoxy)pentanal as a colorless oil (117 mg). The material was used in the following step without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 9.80 (s, 1 H), 7.16 (t, J=8.08 Hz, 1 H), 6.43-6.53 (m, 3 H), 3.89-4.01 (m, 4 H), 2.50-2.57 (m, 2 H), 1.14-1.92 (m, 12 H), 0.92 (t, J=6.69 Hz, 3 H). MS ESI [M+H]+, calcd for [C17H26O3+H]+: 279.2 found m/z 279.2 (95) and 301.1 ([M+Na]+, 100).

Workup

  1. temperatureAfter cooling to rt the reaction mixture
  2. extractionextracted with Et2O (3×)
  3. washwashed (aq NaHCO3, brine)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a11464be266c4addbd4d528db31e42af
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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