Water → 2-(Dimethylaminomethyl)phenyltributylstannyl Ether

HRID 65554Notes

Reaction equation

HRID 65554 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][Sn:5]([O:14][Sn:15]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9].[CH3:28][N:29]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1O)[CH3:30].O>C1C=CC=CC=1>[CH3:28][N:29]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH2:23][CH2:22][CH2:21][CH2:20][Sn:15]([O:14][Sn:5]([CH2:10][CH2:11][CH2:12][CH2:13][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[CH2:31][N:29]([CH3:30])[CH3:28])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][CH2:3][CH2:2][CH3:1])([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:24][CH2:25][CH2:26][CH3:27])[CH3:30]

Participants

5

Reactant 3

HCID 962WaterHCID 328972-((Dimethylamino)methyl)phenolHCID 16682746Bis(tributyltin) oxide

Product 1

HCID 706227372-(Dimethylaminomethyl)phenyltributylstannyl Ether

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-(Dimethylaminomethyl)phenyltributylstannyl Ether is prepared as follows: 59.6 gm (0.1 mole) bis(tributyltin) oxide and 30.0 gm (0.2 mole) 2-dimethylaminomethyl phenol (as just prepared) are placed in 200 ml benzene. This is slowly heated to reflux in a system equipped with a Dean-Starke tube. After about 30 minutes water began to separate in the Dean-Starke tube. After 72 hours at reflux 1.9 ml of water had separated (theory 1.8 ml). A clear straw colored reaction mixture resulted and benzene is evaporated therefrom on a rotating evaporator to provide 87.7 gm of a yellow liquid. This is fractionated at reduced pressure. The product collected at 165°-168° C. at 0.5 mm is 75.0 gm of a straw colored liquid (Percent yield - 82). Infrared spectral analysis provided bands characteristic of the desired product.

Workup

  1. temperatureThis is slowly heated
  2. temperatureto reflux in a system
  3. customequipped with a Dean-Starke tube
  4. customto separate in the Dean-Starke tube
  5. temperatureAfter 72 hours at reflux 1.9 ml of water
  6. customhad separated (theory 1.8 ml)
  7. customA clear straw colored reaction mixture resulted
  8. custombenzene is evaporated
  9. customon a rotating evaporator

Sources & evidence

ORD record
ord-5682a8e924e347948a82054d0c82700d
Source dataset
uspto-grants-1978_12
Patent number
US04128429

Reaction notes

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