Sodium Hydroxide → HCID 23458142, compound

HRID 1679811Notes

Reaction equation

HRID 1679811 reaction equation
[OH:1][CH:2]([CH2:5][CH2:6][CH2:7][CH:8](O)[CH:9]=[CH2:10])[CH:3]=[CH2:4].Cl.[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16]Cl.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][CH:8]([CH2:7][CH2:6][CH2:5][CH:2]([OH:1])[CH:3]=[CH2:4])[CH:9]=[CH2:10]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 23458141HCID 23458141, compound

Product 1

HCID 23458142HCID 23458142, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of 3,7-dihydroxy-nona-1,8-diene (181.5 g; 1.16 M), 2-dimethylaminoethylchloride hydrochloride (201 g; 1.4 M), powdered NaOH (163 g; 4.07 M) and toluene (2.4 l) was refluxed during 4.5 h. The reaction mixture was cooled and washed successively with H2O and sat. brine. Work-up and fractional distillation in vacuo (spinning band) gave the title compound as a colourless oil (142 g) (54%) bp. 85°-90°/0.05 Torr, GC (5% Carbowax®) 240°/4.8 min., RF 0.38 [methanol/EtOAc (9:1]; NMR (δ) 1.5 (c, 6H; aliphatic CH2), 2.21 [s, 6H; (CH3)2N], 2.49 (t, J 7 Hz, 2H; CH2N), 3.16* (bs, 1H, OH), 3.15-4.2 [c, 4H, CH2 (O) and CH(O)] and 4.9-6.2 (c, 6H; olefinic H) (*D2O exchange removes this signal); IR (cm-1) 3400 (b), 3080, 1645, 1460, 995 and 920.

Workup

  1. temperaturewas refluxed during 4.5 h
  2. temperatureThe reaction mixture was cooled
  3. washwashed successively with H2O and sat. brine
  4. distillationfractional distillation in vacuo (spinning band)

Sources & evidence

ORD record
ord-fa2e40f32a394fd59e14b87641738e88
Source dataset
uspto-grants-1981_06
Patent number
US04271048

Reaction notes

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