4-Methoxybenzyl alcohol → HCID 43174158, compound

HRID 475070Notes

Reaction equation

HRID 475070 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][CH:4]=1.[H-].[Na+].Br[CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 68320Ethyl 3-bromopropionate

Product 1

HCID 43174158HCID 43174158, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (4-methoxyphenyl)methanol (76.3 g, 552.4 mmol) in anhydrous toluene (1 L) at 0° C. was added portionwise NaH (27.6 g, 630.5 mmol) over a period of 30 min, followed by ethyl 3-bromopropanoate (100 g, 552.4 mmol). The mixture was stirred at RT for 3 h and then quenched with 20% aqueous NH4Cl (500 mL). The organic layer was separated, and the aqueous layer was extracted with EtOAc (2×500 mL). The combined organic layers were washed with brine, dried (Na2SO4) and then concentrated in vacuo to give ethyl 3-((4-methoxybenzyl)oxy)propanoate (112 g, 85%) as colorless oil.

Workup

  1. customquenched with 20% aqueous NH4Cl (500 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with EtOAc (2×500 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e08baa32b13141178634ffe02938f87a
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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