Water → HCID 131731068, compound

HRID 1910362Notes

Reaction equation

HRID 1910362 reaction equation
[CH2:1]([OH:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH2:10](N(C(C)C)C(C)C)C.[CH2:19]([Si:37](C)(Cl)Cl)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].O>C1(C)C=CC=CC=1>[CH3:10][CH:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:19][SiH:37]1[O:9][CH2:1][C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[O:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 5146Salicyl AlcoholHCID 78835Dichloro(methyl)octadecylsilaneHCID 81531Diisopropylethylamine

Product 1

HCID 131731068HCID 131731068, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
40 °C

Procedure

In a 1 l four-neck flask with stirrer, reflux condenser and dropping funnel, 31.7 g of salicyl alcohol (0.25 mol) and 66.7 g (0.52 mol) of dried N-ethyldiisopropylamine were suspended under argon in 100 ml of anhydrous toluene at 22° C. 110 g of Octadecylmethyldichlorosilane (95%; 0.25 mol) was melted and dissolved in 100 ml of dry toluene. This solution was added dropwise at 23 to 27° C. within 55 minutes, in the course of which an exothermic reaction was observed. Cooling with an ice bath held the reaction temperature at a maximum of 27° C. After the addition had ended, the temperature was raised to 40° C., and exothermicity (without heating to 45° C.) was again observed. The reaction vessel was then cooled to 40° C. with cold water, and it was stirred at this temperature for one hour and then cooled to RT. The suspension was left to stand at RT overnight. The precipitate (hydrochloride) was filtered off with suction through a P40 glass frit under N2, and the filtrate was concentrated by rotary evaporation at 120° C./5 mbar. Yield 80.9 g (77% of theory).

Workup

  1. temperatureIn a 1 l four-neck flask with stirrer, reflux condenser
  2. additionThis solution was added dropwise at 23 to 27° C. within 55 minutes, in the course of which
  3. customan exothermic reaction
  4. temperatureCooling with an ice bath
  5. customat a maximum of 27° C
  6. additionAfter the addition
  7. temperatureexothermicity (without heating to 45° C.)
  8. temperaturecooled to RT
  9. waitThe suspension was left
  10. waitto stand at RT overnight
  11. filtrationThe precipitate (hydrochloride) was filtered off with suction through a P40 glass frit under N2
  12. concentrationthe filtrate was concentrated by rotary evaporation at 120° C./5 mbar

Sources & evidence

ORD record
ord-3f107be11d5d46d38fdf666f3daf389e
Source dataset
uspto-grants-2013_12
Patent number
US08603681B2

Reaction notes

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