Aniline → N,N-Di(6-hydroxyhexyl)aniline

HRID 2291429Notes

Reaction equation

HRID 2291429 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8](=[O:11])([O-])[O-].[K+].[K+].Cl[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21]>>[OH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][N:1]([CH2:4][CH2:3][CH2:2][CH2:7][CH2:6][CH2:8][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 748286-Chloro-1-hexanol

Product 1

HCID 21982671N,N-Di(6-hydroxyhexyl)anilineYield 127%

Procedure

A mixture of freshly distilled aniline (93 g, 1.10 mol), potassium carbonate (304 g, 2.2 mol), 6-chloro-1-hexanol (300.0 g, 2.2 mol), and 500 mL of η-butanol was heated at reflux for 82 hours under nitrogen with vigorous stirring. After cooling and filtering, the butanol was evaporated at reduced pressure to leave a tan oil. The oil was fractionally distilled in vacuo, yielding 205 g (70%) of A1 as a colorless oil, bp 195°-225° C. (0.15 nm).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 82 hours under nitrogen with vigorous stirring
  3. temperatureAfter cooling
  4. filtrationfiltering
  5. customthe butanol was evaporated at reduced pressure
  6. customto leave a tan oil
  7. distillationThe oil was fractionally distilled in vacuo

Sources & evidence

ORD record
ord-405f877d462048c0833a911c51b535a3
Source dataset
uspto-grants-1989_01
Patent number
US04796971

Reaction notes

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