Sodium Hydroxide → 4-Propylbenzoic acid

HRID 443681

Reaction equation

HRID 443681 reaction equation
Br[O-:2].[Na+].BrBr.[OH-].[Na+].[CH3:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](C)=[O:18])=[CH:13][CH:12]=1>O.O1CCOCC1>[CH2:10]([C:11]1[CH:12]=[CH:13][C:14]([C:17]([OH:18])=[O:2])=[CH:15][CH:16]=1)[CH2:9][CH3:8]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 762361-(4-Propylphenyl)ethan-1-oneHCID 23673712Sodium hypobromite

Product 1

HCID 1376014-Propylbenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of sodium hypobromite prepared by dissolving bromine (1.0 mole) in a solution of sodium hydroxide (3.5 mole) in water (700 ml) at 0° C. was added to a well stirred solution of 4-n-propylacetophenone (0.2 mole), prepared in step A1, in dioxan (500 ml). Throughout the addition and for 0.25 hours afterwards the temperature was maintained at 35°-45° C. The excess of sodium hypobromite wad destroyed by adding a solution of sodium metabisulphite. Water (3.5 L) was added and bromoform distilled from the reation mixture. On cooling, the solution was acidified with concentrated hydrochloric acid and the precipitated product filtered off and washed with water. The product was crystallised from ethanol/water to yield white crystals mpt 141.2° C.

Workup

  1. additionwas added to a well
  2. additionThroughout the addition
  3. temperaturefor 0.25 hours afterwards the temperature was maintained at 35°-45° C
  4. customThe excess of sodium hypobromite wad destroyed
  5. additionby adding a solution of sodium metabisulphite
  6. additionWater (3.5 L) was added
  7. distillationbromoform distilled from the reation mixture
  8. temperatureOn cooling
  9. filtrationthe precipitated product filtered off
  10. washwashed with water
  11. customThe product was crystallised from ethanol/water

Sources & evidence

ORD record
ord-2a6785196dc94b86ba2f8bd7a322ec51
Source dataset
uspto-grants-1981_04
Patent number
US04261651

Linked notes

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