Hydrochloric Acid → HCID 59560834, compound

HRID 1176961Notes

Reaction equation

HRID 1176961 reaction equation
[CH2:1]([SH:5])[CH2:2][CH2:3][SH:4].[CH2:6]([O:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:22]=O)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].Cl>C(Cl)(Cl)Cl>[CH2:6]([O:18][C:19]1[CH:20]=[C:21]([CH:22]2[S:5][CH2:1][CH2:2][CH2:3][S:4]2)[CH:24]=[CH:25][C:26]=1[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 80131,3-PropanedithiolHCID 27249313,4-Bis(dodecyloxy)benzaldehyde

Product 1

HCID 59560834HCID 59560834, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1,3-propanedithiol (4.7 mL, 46.8 mmol) was added to a solution of 3,4-bis(dodecyloxy)benzaldehyde (20.0 g, 42.1 mmol) in 100 mL of chloroform. The reaction mixture was stirred at room temperature for 2 h. Concentrated hydrochloric acid (1.5 mL) was added to the mixture and the mixture was stirred at room temperature for additional 2 h. The mixture was washed with water and a saturated aqueous NaCl solution several times. The organic phase was dried over anhydrous MgSO4. The solvent was removed under reduced pressure and the product was further dried under vacuum at 47° C. overnight to give an off-white solid (22.7 g, 95%). mp 73-75° C. 1H NMR (200 MHz, CDCl3, δ): 6.91-7.00 (m, 2H), 6.78 (d, J=7.8 Hz, 1H), 5.08 (s, 1H), 3.96 (q, J=6.2 Hz, 4H), 2.80-3.12 (m, 4H), 1.89-2.21 (m, 2H), 1.78 (m, 4H), 1.42 (m, 4H), 1.24 (s, 32H), 0.86 (t, J=6.2 Hz, 6H). 13C{1H} NMR (50 MHz, CDCl3, δ): 149.12, 131.56, 120.02, 113.52, 113.14, 69.12, 51.19, 32.15, 31.86, 29.57, 29.36, 29.30, 29.20, 25.97, 25.04, 22.63, 14.05. IR (cm−1): 2916, 2847, 1586, 1517, 1466, 1269, 1137. HRMS-FAB (m/z): [M+H]+ calcd for C34H61O2S2, 565.4113; found, 565.4087. Anal. Calcd for C34H60O2S2: C, 72.28; H, 10.70. Found: C, 72.47; H, 10.78.

Workup

  1. stirringthe mixture was stirred at room temperature for additional 2 h
  2. washThe mixture was washed with water
  3. dry with materialThe organic phase was dried over anhydrous MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customthe product was further dried under vacuum at 47° C. overnight

Sources & evidence

ORD record
ord-f803110df0c34894ba212816650b0daf
Source dataset
uspto-grants-2010_11
Patent number
US07842830B2

Reaction notes

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