Sodium Bicarbonate → 1-[2-Hydroxy-5-(2-hydroxyethyl)phenyl]ethan-1-one

HRID 26672Notes

Reaction equation

HRID 26672 reaction equation
C([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([C:14](=[O:16])[CH3:15])[CH:8]=1)(=O)C.C(=O)(O)[O-].[Na+]>C(O)C.O>[C:14]([C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[OH:13])[CH2:6][CH2:5][OH:4])(=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 127698062-(3-Acetyl-4-hydroxyphenyl)ethyl acetate

Product 1

HCID 127698071-[2-Hydroxy-5-(2-hydroxyethyl)phenyl]ethan-1-oneYield 108.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-(3-acetyl-4-hydroxyphenyl)ethyl acetate (35.7 g) in ethanol (400 ml), and sodium bicarbonate (42 g) in water (200 mls) was refluxed for 81/2 hours. The ethanol was removed on a `Rotavapor` and the residue was extracted with ether (3x). The combined ethereal extracts were washed with water, sodium bicarbonate solution, saturated brine solution, dried over anhydrous magnesium sulphate, and evaporated to yield a red oil (31.3 g). The oil was recrystallised from hexane and ether (4:1) to yield the product as a pale yellow crystalline solid (18.3 g). The mother liquors were concentrated and an additional batch of product was obtained as a pale yellow crystalline solid (9.3 g).

Workup

  1. customThe ethanol was removed on a `Rotavapor` and the residue
  2. extractionwas extracted with ether (3x)
  3. washThe combined ethereal extracts were washed with water, sodium bicarbonate solution, saturated brine solution
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-2d50ac568846435595ec3de54eebe546
Source dataset
uspto-grants-1979_04
Patent number
US04151179

Reaction notes

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