Hydrochloric Acid → HCID 66654549, compound

HRID 926667Notes

Reaction equation

HRID 926667 reaction equation
[CH2:1]([CH:7]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:8][CH2:9][C:10]1[CH:15]=[C:14]([O:16]C)[C:13]([CH2:18][CH2:19][CH:20]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:12][C:11]=1[O:35]C)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].B(Br)(Br)Br.CO.Cl>ClCCl.O>[CH2:29]([CH:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:19][CH2:18][C:13]1[CH:12]=[C:11]([OH:35])[C:10]([CH2:9][CH2:8][CH:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])=[CH:15][C:14]=1[OH:16])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 25134Boron tribromideHCID 68028053HCID 68028053, compound

Product 1

HCID 66654549HCID 66654549, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

1,4-Bis-(3-hexyl-undecyl)-2,5-dimethoxy-benzene (7.000 g; 11.38 mmol) is dissolved in anhydrous dichloromethane (115 cm3) before cooling down the solution to −78° C. Neat boron tribromide (2.69 ml; 28.5 mmol) is added dropwise over 15 minutes. The resulting mixture is stirred at −78° C. for 1 hour before being warmed to 23° C. for 18 hours. Methanol (25 cm3) and then diluted HCl (75 cm3) is added before pouring the reaction mixture into water. The organic layer is separated and the aqueous layer extracted tow times with diethyl ether (2×250 cm3). The organic fractions are combined, dried over magnesium sulfate and the solvents removed under vacuum. The crude product is used, as it, without further purification (6.51 g, Yield: 97%). NMR (1H, 300 MHz, CDCl3): δ 6.54 (s, 2H); 4.24 (br, 2H); 2.47 (m, 4H); 1.51 (m, 4H); 1.26 (m; 50H); 0.88 (t, J=6.7 Hz, 12H).

Workup

  1. temperaturebefore being warmed to 23° C. for 18 hours
  2. customThe organic layer is separated
  3. extractionthe aqueous layer extracted tow times with diethyl ether (2×250 cm3)
  4. dry with materialdried over magnesium sulfate
  5. customthe solvents removed under vacuum
  6. customThe crude product is used, as it, without further purification (6.51 g, Yield: 97%)

Sources & evidence

ORD record
ord-1c7f548f85a94bb4a525f3ba4af92e03
Source dataset
uspto-grants-2016_03
Patent number
US09287504B2

Reaction notes

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