Oxygen → Tert-butyl 4-(2-hydroxyethyl)benzoate

HRID 1913771Notes

Reaction equation

HRID 1913771 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15](O)=[O:16])=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O=O.[Cl-].[NH4+]>C1COCC1>[OH:16][CH2:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 977OxygenHCID 25517Ammonium ChlorideHCID 598545182-(4-(Tert-butoxycarbonyl)phenyl)acetic acid

Product 1

HCID 10331132Tert-butyl 4-(2-hydroxyethyl)benzoateYield 94.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

30.47 ml (30.47 mmol) of 1 M borane-THF complex solution are slowly added dropwise to a solution of 3.6 g (15.24 mmol) of [4-(tert-butoxycarbonyl)phenyl]acetic acid in 100 ml of THF at −10° C. with exclusion of oxygen. The mixture is stirred at 0° C. for 4 hours. Subsequently, ammonium chloride solution is added and the mixture is extracted with diethyl ether. The combined organic phases are washed with sodium chloride solution, dried over sodium sulphate and evaporated. 3.2 g (14.4 mmol, 92% yield) of the title compound are obtained.

Workup

  1. extractionthe mixture is extracted with diethyl ether
  2. washThe combined organic phases are washed with sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-4a45988258714cbbb3afedd7d9554251
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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