HCID 14937397, compound → HCID 15399808, compound

HRID 2120022Notes

Reaction equation

HRID 2120022 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])(=O)C.[CH2:18]([O:24][C:25]1[CH:26]=[C:27]([C:38]2[CH:43]=[CH:42][C:41]([O:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[C:40]([O:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH:39]=2)[CH:28]=[CH:29][C:30]=1[O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>ClCCl.[Fe](Cl)Cl>[OH:4][C:5]1[C:6]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:7][C:8]2[C:43]3[C:38](=[CH:39][C:40]([O:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])=[C:41]([O:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH:42]=3)[C:27]3[C:28](=[CH:29][C:30]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[C:25]([O:24][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:26]=3)[C:9]=2[CH:10]=1

Participants

5

Reactant 2

HCID 14937397HCID 14937397, compoundHCID 23437329HCID 23437329, compound

Product 1

HCID 15399808HCID 15399808, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 24458Ferrous ChlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Anhydrous iron chloride (4.7 g, 28.9 mmol) was added to a stirred mixture of 2-acetoxy-1-hexyloxybenzene (3.4 g, 14.4 mmol) and 3,3′,4,4′-tetrahexyloxybiphenyl (4.0 g, 7.2 mmol) in dichloromethane. The mixture was stirred for 5 h and poured onto methanol (300 ml). The resultant precipitate was filtered off and saponified with potassium carbonate in ethanol (5% water) under reflux for over night. After cooling, water (50 ml) was added and the product was extracted with dichloromethane, dried (MgSO4), concentrated and purified by column chromatography on silica gel using dichloromethane and petroleum spirit (1:1) as eluent and then recrystallised from ethanol to yield a white solid (3.59 g, 67%). Found: C, 77.30; H, 9.85. C48H72O6 requires C, 77.38; H, 9.74. δH (CHCl3) 7.96 (s, 1H, ArH), 7.83-7.82 (m, 4H, ArH), 7.77 (s, 1H, ArH), 5.92 (1H, s, OH), 4.31-4.18 (m, 10H, OCH2), 1.99-1.92 (m, 10H, CH2), 1.58-1.55 (m, 10H, CH2), 1.46-1.38 (m, 20H, CH2), 0.97-0.83 (15H, m, CH3).

Workup

  1. additionpoured onto methanol (300 ml)
  2. filtrationThe resultant precipitate was filtered off
  3. temperatureunder reflux for over night
  4. temperatureAfter cooling
  5. additionwater (50 ml) was added
  6. extractionthe product was extracted with dichloromethane
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. custompurified by column chromatography on silica gel
  10. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-2bd98c1d2c6d4a1693d27025ae786f9c
Source dataset
uspto-grants-2004_02
Patent number
US06689290B2

Reaction notes

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