Diethyl Ether → Tert-butyl 4-(2-hydroxyethyl)benzoate

HRID 742311Notes

Reaction equation

HRID 742311 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.C[Mg]Br.[Cl-].[NH4+].[CH2:21]([O:23]CC)C>>[OH:23][CH2:21][CH2:1][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

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 2751588Tert-butyl 4-formylbenzoateHCID 178418573HCID 178418573, compound

Product 1

HCID 10331132Tert-butyl 4-(2-hydroxyethyl)benzoate

Procedure

t-Butyl p-formylbenzoate (20 g, 97 mmol) was dissolved in dry diethyl ether (300 ml), followed by the dropwise addition of methylmagnesium bromide (3M ethereal solution, 33 ml) under cooling with ice and stirring. The obtained mixture was stirred for one hour and poured into a saturated aqueous solution of ammonium chloride, and the obtained mixture was extracted with ether. The ethereal phase was washed with water, dried and distilled to remove the solvent. The pale-yellow viscous liquid residue thus obtained was subjected to silica gel column chromatography and eluted with a solvent (ethyl acetate/hexane=1:4) to give 21.8 g of t-butyl 4-(hydroxyethyl)benzoate.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe obtained mixture was stirred for one hour
  3. extractionthe obtained mixture was extracted with ether
  4. washThe ethereal phase was washed with water
  5. customdried
  6. distillationdistilled
  7. customto remove the solvent
  8. customThe pale-yellow viscous liquid residue thus obtained
  9. washeluted with a solvent (ethyl acetate/hexane=1:4)

Sources & evidence

ORD record
ord-26d77fb2859b41c29114d3324934a4fb
Source dataset
uspto-grants-1996_09
Patent number
US05554615

Reaction notes

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