Water → 4-Tetradecyloxyphenyl-benzyl ketone

HRID 1902370Notes

Reaction equation

HRID 1902370 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 545317394-Tetradecyloxyphenyl-benzyl ketoneYield 167%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ea6a4400a0d248f7908cd31e1789250d
Source dataset
uspto-grants-1982_12
Patent number
US04362878

Reaction notes

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