1-Bromooctane → HCID 15250385, compound

HRID 486976Notes

Reaction equation

HRID 486976 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:24]([OH:31])=[C:23]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:22]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].Br[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[C:27]([C:25]1[CH:26]=[C:21]([CH2:20][CH2:19][N:18]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:17][CH2:16][C:7]2[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]([OH:11])=[C:9]([C:12]([CH3:13])([CH3:15])[CH3:14])[CH:8]=2)[CH:22]=[C:23]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:24]=1[OH:31])([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 81401-Bromooctane2×HCID 10340Sodium CarbonateHCID 15250384HCID 15250384, compound

Product 1

HCID 15250385HCID 15250385, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Stir a solution of 4.5 g (9.3 mmols) of N,N-bis[β-(3,5-di-t-butyl-4-hydroxyphenyl)ethyl]amine, 1.8 g (9.3 mmols) of 1-bromooctane, and 2.0 g (18.7 mmols) of sodium carbonate in 50 mL of acetonitrile for 17 hours at reflux temperature. Add another 0.3 g (1.6 mmols) of 1-bromooctane and stir at reflux for an additional 18 hours. After cooling, concentrate the reaction mixture, in vacuo, dissolve the resulting oil in 50 mL of toluene, and wash with water (2×50 mL). Dry the organic phase over magnesium sulfate and concentrate in vacuo. Flash column chromatography (120 g silica gel 60, 230-400 mesh, EM), using heptane followed by 1.5% isopropyl alcohol/heptane as the eluting solvents, gives 3.3 g (60.0%) of N,N-bis[β-(3,5-di-t-butyl-4-hydroxyphenyl)ethyl]octylamine as a slightly colored oil which GC area % analysis shows to be 99.0% pure.

Workup

  1. temperatureat reflux temperature
  2. temperatureat reflux for an additional 18 hours
  3. temperatureAfter cooling
  4. concentrationconcentrate the reaction mixture
  5. dissolutionin vacuo, dissolve the resulting oil in 50 mL of toluene
  6. washwash with water (2×50 mL)
  7. dry with materialDry the organic phase over magnesium sulfate
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-6bdeff3360e04341a88b4ef283a52aba
Source dataset
uspto-grants-1994_03
Patent number
US05292956

Reaction notes

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