Water → 4-Tetradecyloxyphenyl-benzyl ketone

HRID 128340

Reaktionsgleichung

Reaktionsgleichung von HRID 128340
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]([CH:17]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:16])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[OH-].[K+].[CH2:33](Br)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46].O>C(O)C>[CH2:33]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]([CH:17]([C:24]2[CH:25]=[CH:26][C:27]([O:30][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:15][CH2:8][CH2:5][CH2:4][CH2:3][CH2:2][CH2:7][CH3:6])=[CH:28][CH:29]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:16])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8208Myristyl bromideHCID 14797Potassium HydroxideHCID 542796974-Hydroxyphenyl-benzyl ketone

Produkt 1

HCID 545317394-Tetradecyloxyphenyl-benzyl ketoneAusbeute 167 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 4-hydroxyphenyl-benzyl ketone (10.5 g) in a solution of potassium hydroxide (3.0 g) in ethanol (100 ml) was added tetradecylbromide (16 g). The reaction mixture was stirred at gentle reflux temperature for 12 hours, cooled and poured into water. The product was extracted into chloroform, washed further with water, dried over MgSO4, filtered and evaporated. Recrystallisation of the residue from methanol gave the above compound as a colourless crystalline solid (17.5 g, 86%) m.p. 72°-74° C.

Aufarbeitung

  1. temperaturecooled
  2. extractionThe product was extracted into chloroform
  3. washwashed further with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customRecrystallisation of the residue from methanol

Quellen und Nachweise

ORD-Eintrag
ord-ec660a57485844979109636ce79943c1
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04259437

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