1-Bromopentane → HCID 19885189, compound

HRID 846254Notes

Reaction equation

HRID 846254 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=[O:12])[CH3:11])=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[OH-].[Na+]>O>[CH2:16]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10](=[O:12])[CH3:11])=[CH:6][CH:7]=1)[CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 80571-BromopentaneHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 216484-(4'-Hydroxyphenyl)-2-butanone

Product 1

HCID 19885189HCID 19885189, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(4-Hydroxyphenyl)-2-butanone (49 g) was added by portions while warming to a stirred solution of potassium hydroxide (0.33 m) in 15 ml of water. To this was added dropwise, 49.8 g of 1-bromopentane and the resultant mixture was stirred at reflux temperature overnight. The mixture was allowed to cool after which 500 ml of 20% sodium hydroxide was added and the resultant mixture was stirred an additional 30 minutes followed by extraction with ethylacetate. The organic extracts were dried and evaporated to yield approximately 63 g of the desired 4-(4-pentoxyphenyl)-2-butanone which was used to prepare the title compound as follows.

Workup

  1. additionTo this was added dropwise
  2. temperatureat reflux temperature overnight
  3. additionwas added
  4. extractionfollowed by extraction with ethylacetate
  5. customThe organic extracts were dried
  6. customevaporated

Sources & evidence

ORD record
ord-2cac44acbb5044e2b3b6221d8c42bb00
Source dataset
uspto-grants-1992_08
Patent number
US05135955

Reaction notes

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