Tetrahydrofuran → Methyl 4-(1-hydroxyethyl)benzoate

HRID 1729134Notes

Reaction equation

HRID 1729134 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].O1CCCC1.B.[Na]>C(O)C>[OH:3][CH:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 137990Methyl 4-acetylbenzoateHCID 178418435HCID 178418435, compound

Product 1

HCID 586417Methyl 4-(1-hydroxyethyl)benzoateYield 98.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

71.2 g (0.4 mol) of methyl 4-acetylbenzoate, 300 ml tetrahydrofuran and 100 ml of ethanol were supplied into a four-necked flask equipped with a stirrer and a thermometer. Then 7.6 g (0.2 mol) of sodium boron hydride was added at 15°-25° C. over a period of 3 hours. The mixture was maintained at the same temperature for 5 hours and the resulting reaction solution was poured into ice-water and extracted twice with 400 ml of ethyl acetate. The organic layer was concentrated under reduced pressure to obtain 71.0 g of methyl 4-(1-hydroxyethyl)benzoate (IIII-1) in a 98.6% yield.

Workup

  1. customequipped with a stirrer
  2. temperatureThe mixture was maintained at the same temperature for 5 hours
  3. customthe resulting reaction solution
  4. extractionextracted twice with 400 ml of ethyl acetate
  5. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-afff6d6157c742d08f06521bd5e5cc35
Source dataset
uspto-grants-1994_07
Patent number
US05332675

Reaction notes

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