Methanol → Bis(trihexylsiloxy)silicon 2,3-naph- thalocyanine

HRID 1589054Notes

Reaction equation

HRID 1589054 reaction equation
[CH2:1]([Si:7]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[OH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C[O-].[Na+].[CH:24]1[CH:29]=[C:28]2[C:30]3[N-:63][C:62]([C:27]2=[CH:26][CH:25]=1)=[N:61][C:59]1=[N:60][C:52]([C:53]2[C:58]1=[CH:57][CH:56]=[CH:55][CH:54]=2)=[N:51][C:49]1=[N:50][C:42]([C:43]2[C:48]1=[CH:47][CH:46]=[CH:45][CH:44]=2)=[N:41][C:39]1[N-:40][C:32](=[C:33]2[C:38]=1[CH:37]=[CH:36][CH:35]=[CH:34]2)[N:31]=3.[Si+4:64].[Cl-].[Cl-].CO>C(O)C>[CH3:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][Si:7]([O-:8])([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][Si:7]([O-:8])([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH:2]1[CH:1]=[C:35]2[C:36]([CH:37]=[C:38]3[C:39]4[N-:40][C:32](=[N:31][C:30]5[N-:63][C:62]([N:61]=[C:59]6[N:60]=[C:52]([N:51]=[C:49]7[N:50]=[C:42]([N:41]=4)[C:43]4[C:48]7=[CH:47][C:46]7[C:45]([CH:44]=4)=[CH:17][CH:18]=[CH:19][CH:20]=7)[C:53]4[C:58]6=[CH:57][C:56]6[C:55]([CH:54]=4)=[CH:9][CH:10]=[CH:11][CH:12]=6)=[C:27]4[C:28]=5[CH:29]=[C:24]5[C:25](=[CH:26]4)[CH:15]=[CH:16][CH:17]=[CH:18]5)[C:33]3=[CH:34]2)=[CH:4][CH:3]=1.[Si+4:64]

Participants

6

Reactant 4

HCID 887MethanolHCID 163603TRIHEXYLSILANOLHCID 10942334Sodium MethoxideHCID 178478905HCID 178478905, compound2×

Product 1

HCID 163602Bis(trihexylsiloxy)silicon 2,3-naph- thalocyanineYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of tri-n-hexylsilanol (14.9 g), sodium methoxide (2.67 g) and absolute ethanol (50 ml) was reduced to an oil under vacuum. This oil was added to a mixture of dichlorosilicon phthalocyanine (Formula 9, from Aldrich Chemical CO., Milwaukee, Wis., 15.10 g) and distilled, dry 1,2,4-trimethyl-benzene (70 ml). The resulting suspension was refluxed for 1 hr and was filtered hot using Whatman #54 filter paper. The filtrate was allowed to cool (12 hr) and was diluted with methanol (350 mol). The precipitated product of Formula 10 was isolated by filtration, washed with methanol (100 ml) and vacuum dried at room temperature overnight, (22.06 g, 79% yield) m.pt. 175° C.; IR (Nujol) 1525 (s), 1325 (s), 1125(s), 1080 (s), 1038 (s, Si--O--Si), 725 (s) cm-1.

Workup

  1. distillationdistilled
  2. temperatureThe resulting suspension was refluxed for 1 hr
  3. filtrationwas filtered hot
  4. filtrationfilter paper
  5. temperatureto cool (12 hr)

Sources & evidence

ORD record
ord-4dcde6f944384596b06f072e41fafb48
Source dataset
uspto-grants-1993_06
Patent number
US05224196

Reaction notes

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