4-Hydroxybenzyl Alcohol → HCID 54575563, compound

HRID 1428965Notes

Reaction equation

HRID 1428965 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)=[O:4].[OH:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][OH:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH:19][CH2:18][C:17]1[CH:20]=[CH:21][C:14]([O:13][CH2:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=2)=[O:4])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 11430Potassium CarbonateHCID 101294Bromomethyl 3-methoxyphenyl ketone

Product 1

HCID 54575563HCID 54575563, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirring solution of 2-bromo-3′-methoxyacetophenone (3.00 g, 13.1 mmol; Supplier=Kalexsyn; Lot=803-TTP-145) in acetone (30 ml) was added 4-hydroxybenzylalcohol (1.69 g, 13.6 mmol) and potassium carbonate (1.88 g, 13.6 mmol). The resulting mixture was stirred at RT overnight. The reaction mixture was partitioned between water and EtOAc, and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The product was analyzed on a large Biotage column eluting with 50% EtOAc/hexanes. Fractions containing product were combined and evaporated in vacuo to give 2.98 g of the title compound as a white solid.

Workup

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. extractionthe aqueous phase was extracted with EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. washeluting with 50% EtOAc/hexanes
  8. additionFractions containing product
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-d87dcc23d41849ae9edfe411c33c17cc
Source dataset
uspto-grants-2015_01
Patent number
US08937182B2

Reaction notes

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