Methanol → HCID 66593067, compound

HRID 582281Notes

Reaction equation

HRID 582281 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]2=[N:6][N:7]([C:9]3[CH:14]=[C:13]([CH2:15][CH2:16][OH:17])[CH:12]=[C:11]([CH2:18]N(CC)CC)[C:10]=3[OH:24])[N:8]=[C:4]2[CH:3]=1.[Cl:27][C:28]1[CH:46]=[CH:45][C:31]2=[N:32][N:33]([C:35]3[CH:40]=[C:39]([CH2:41][CH2:42][OH:43])[CH:38]=[CH:37][C:36]=3[OH:44])[N:34]=[C:30]2[CH:29]=1.CO.C[O-].[Na+]>C1(C)C(C)=CC=CC=1>[CH2:18]([C:37]1[CH:38]=[C:39]([CH2:41][CH2:42][OH:43])[CH:40]=[C:35]([N:33]2[N:32]=[C:31]3[CH:45]=[CH:46][C:28]([Cl:27])=[CH:29][C:30]3=[N:34]2)[C:36]=1[OH:44])[C:11]1[CH:12]=[C:13]([CH2:15][CH2:16][OH:17])[CH:14]=[C:9]([N:7]2[N:6]=[C:5]3[CH:25]=[CH:26][C:2]([Cl:1])=[CH:3][C:4]3=[N:8]2)[C:10]=1[OH:24]

Participants

6

Reactant 4

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 53790982HCID 53790982, compoundHCID 544779472-(5-chloro-2H-benzotriazole-2-yl)-4-(2-hydroxyethyl)phenol

Product 1

HCID 66593067HCID 66593067, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In 100 ml of xylene were dissolved 37.0 g (93.9 mmols) of crude 2-(5-chloro-2H-benzotriazole-2-yl)-4-(2-hydroxyethyl)-6-(N,N-diethylaminomethyl)phenol synthesized in Example 10 and 27.2 g (93.9 mmols) of the purified product of 2-(5-chloro-2H-benzotriazole-2-yl)-4-(2-hydroxyethyl)phenol synthesized in Example 7. 5 ml of methanol solution of 28% sodium methylate was added, and the mixture was refluxed in a nitrogen stream for 10 hours. The subsequent treatment was carried out in the same manner as in Example 12, giving 30.8 g of 2,2'-methylenebis[6-(5-chloro-2H-benzotriazole-2-yl)-4-(2-hydroxyethyl)phenol] as pale yellow crystals (yield 55.0%, purity 99.0%).

Workup

  1. temperaturethe mixture was refluxed in a nitrogen stream for 10 hours

Sources & evidence

ORD record
ord-ba63d5c84ee04451bf0a1684b16ebe82
Source dataset
uspto-grants-1999_07
Patent number
US05922882

Reaction notes

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