3-Hydroxybenzyl alcohol → HCID 54044017, compound

HRID 744129Notes

Reaction equation

HRID 744129 reaction equation
[K].[OH:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][OH:7].Br[C:12]1[CH:13]=[C:14]([O:18][CH3:19])[CH:15]=[CH:16][CH:17]=1>CN1C(=O)CCC1.O.[Cu]Cl>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][OH:7]

Participants

7

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 169713-BromoanisoleHCID 5462222Potassium

Product 1

HCID 54044017HCID 54044017, compoundYield 52.1%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
170 °C

Procedure

To a solution of the potassium salt of 3-hydroxybenzyl alcohol (8.1 g, 50 mmol) in N-methyl pyrolidinone (20 ml) were added 3-bromoanisole (11.22 g, 60 mmol), copper (I) chloride (0.1 g, 1 mmol) and p-hydroxyquinoline (0.1 g, 1 mmol) and the reaction was heated to 170° C. for fifty hours. The reaction was cooled to room temperature, diluted with water (150 ml) and extracted with ether (5×50 ml). The combined extracts were dried (MgSO4) and evaporated. The residue was purified by flash chromatography (eluting with 10% ethyl acetate/60°-80° petrol) to afford 3-(3-methoxyphenoxy)benzyl alcohol as a pale oil 6.0 g (52%); a (CDCl3) 3.80 (3H, s, OCH3), 4.64 (2H, s, CH2OH), 6.54-6.70 (3H, m, ArH), 6.88-7.10 (3H, m, ArH), 7.18-7.36 (2H, m, ArH).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with ether (5×50 ml)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by flash chromatography (eluting with 10% ethyl acetate/60°-80° petrol)

Sources & evidence

ORD record
ord-6953ee0b1f004f9eb44bd610e7e57ee6
Source dataset
uspto-grants-1996_09
Patent number
US05559125

Reaction notes

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