Water → HCID 131731068, compound

HRID 1192453Notes

Reaction equation

HRID 1192453 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
45 °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. Octadecylmethyldichlorosilane (95%) was melted and dissolved in 100 ml of dry toluene. This solution was added dropwise at 23 to 27° C. over 55 minutes, in the course of which an exothermic reaction was observed. By cooling with an ice bath, the reaction temperature was kept at not more than 27° C. After the addition had ended, the temperature was raised to 40° C., in the course of which exothermicity (without heating to 45° C.) was again observed. The reaction vessel was then cooled to 40° C. with cold water, and the mixture 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 under N2 through a P40 glass frit, 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. over 55 minutes, in the course of which
  3. customan exothermic reaction
  4. temperatureBy cooling with an ice bath
  5. customwas kept at not more than 27° C
  6. additionAfter the addition
  7. temperaturecooled to RT
  8. waitThe suspension was left
  9. waitto stand at RT overnight
  10. filtrationThe precipitate (hydrochloride) was filtered off with suction under N2 through a P40 glass frit
  11. concentrationthe filtrate was concentrated by rotary evaporation at 120° C./5 mbar

Sources & evidence

ORD record
ord-33ff9df538b24c3b8b06d90ebf14b278
Source dataset
uspto-grants-2014_03
Patent number
US08680203B2

Reaction notes

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