2-Ethylhexyl glycidyl ether → HCID 136395941, compound

HRID 2293006Notes

Reaction equation

HRID 2293006 reaction equation
[C:1]1([CH3:31])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=2[OH:22])[N:12]=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:24]=2[OH:30])[N:10]=1.[CH2:32]([O:36][CH2:37][CH:38]([CH2:43][CH3:44])[CH2:39][CH2:40][CH2:41][CH3:42])[CH:33]1[O:35][CH2:34]1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C1(C)C=C(C)C=C(C)C=1.C(OCC)(=O)C>[C:1]1([CH3:31])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:9]1[N:10]=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:34][CH:33]([OH:35])[CH2:32][O:36][CH2:37][CH:38]([CH2:43][CH3:44])[CH2:39][CH2:40][CH2:41][CH3:42])=[CH:25][C:24]=2[OH:30])[N:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:34][CH:33]([OH:35])[CH2:32][O:36][CH2:37][CH:38]([CH2:43][CH3:44])[CH2:39][CH2:40][CH2:41][CH3:42])=[CH:17][C:16]=2[OH:22])[N:14]=1

Participants

6

Reactant 2

HCID 171622-Ethylhexyl glycidyl etherHCID 135845402HCID 135845402, compound2×

Product 1

HCID 136395941HCID 136395941, compoundYield 81.9%

Reagents, catalysts & solvents 3

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 7947MesityleneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 39.5 g (0.095 mol) of 2-mesityl-4,6-bis(2,4-dihydroxyphenyl)-1,3,5-triazine (compound 1b), 40.7 g (0.2185 mol) of 2-ethylhexyl glycidyl ether (purity 98%) and 3.5 g (9.5 mmol) of ethyltriphenylphosphonium bromide (purity 97%) in 250 ml of mesitylene (purity 99%) is stirred at 140° C. under nitrogen for 16 hours. The clear solution is freed from solvent under reduced pressure. The crude product is dissolved in 200 ml of ethyl acetate and filtered through a 6.0 cm layer of silica gel 60 (230-400 mesh) of diameter 8.0 cm, with elution with 1000 ml of ethyl acetate. Removal of the solvent and drying for 2 hours at 100° C. and a pressure of 0.6 mmHg (80 Pa) give 61.3 g (yield 81.8%) of the title product (compound 7; Tg 54.4° C.) of the formula ##STR106## where R=CH2 --CH(OH)--CH2O--CH2 --CH(C2 H5)--CH2CH2CH2CH3.

Workup

  1. filtrationfiltered through a 6.0 cm layer of silica gel 60 (230-400 mesh) of diameter 8.0 cm, with elution with 1000 ml of ethyl acetate
  2. customRemoval of the solvent
  3. customdrying for 2 hours at 100° C.

Sources & evidence

ORD record
ord-af18eca515804f41ae0c641590a67a28
Source dataset
uspto-grants-1997_11
Patent number
US05686233

Reaction notes

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