Ammonium Chloride → tert-Butyl 4-(1-hydroxypropyl)benzoate

HRID 2294100Notes

Reaction equation

HRID 2294100 reaction equation
[CH:1]([C:3]1[CH:15]=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[CH:5][CH:4]=1)=[O:2].[CH2:16]([Mg]Br)[CH3:17].[Cl-].[NH4+]>CCOCC>[OH:2][CH:1]([C:3]1[CH:15]=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])=[CH:5][CH:4]=1)[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2751588Tert-butyl 4-formylbenzoateHCID 178418443HCID 178418443, compound

Product 1

HCID 21473763tert-Butyl 4-(1-hydroxypropyl)benzoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

t-Butyl p-formylbenzoate (20 g, 97 mmol) was dissolved in ether (300 ml), followed by the dropwise addition of ethylmagnesium bromide (3M ethereal solution, 33 ml) under cooling with ice. The obtained mixture was stirred to complete a reaction. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride and the obtained mixture was extracted with ether. The organic phase was distilled to remove the solvent and the obtained residue was subjected to silica gel column chromatography and eluted with a solvent (ethyl acetate/hexane=1:4) to give 22.3 g of t-butyl 4-(1-hydroxypropyl)benzoate. This product was dissolved in petroleum ether (500 ml), followed by the addition of active manganese dioxide (165 g). The obtained mixture was heated under reflux for 30 hours to complete a reaction. The reaction mixture was filtered and the filtrate was concentrated to give 21.1 g of t-butyl 4-propionylbenzoate.

Workup

  1. temperatureunder cooling with ice
  2. customa reaction
  3. extractionthe obtained mixture was extracted with ether
  4. distillationThe organic phase was distilled
  5. customto remove the solvent
  6. washeluted with a solvent (ethyl acetate/hexane=1:4)

Sources & evidence

ORD record
ord-bfc2ab97b99c4752a13b0f8a8bb83a79
Source dataset
uspto-grants-1997_11
Patent number
US05688800

Reaction notes

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