Tetrahydrofuran → Methyl 4-(2-hydroxyethyl)benzoate

HRID 970827Notes

Reaction equation

HRID 970827 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH2:11])=[CH:6][CH:5]=1.B1C2CCCC1CCC2.[O:22]1CCCC1>>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:22])=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 789669-Borabicyclo(3.3.1)nonaneHCID 583124Methyl 4-ethenylbenzoate

Product 1

HCID 14078904Methyl 4-(2-hydroxyethyl)benzoateYield 64.7%

Conditions

Temperature
0 °C

Procedure

Methyl-4-vinylbenzoate 70 (2.270 g, 14.00 mmol) was dissolved in 50ml of tetrahydrofuran and cooled to 0° C. 9-BBN (0.5M in THF)(28.00 ml, 14.00 mmol) was added and the mixture was stirred for 2 hours. The solution was allowed to warm to room temperature and stirred for an additional 2 hours. The reaction was cooled to 0° C. and quenched with alkaline hydrogen peroxide. The mixture was then extracted with diethyl ether. The extracts were dried over anhydrous sodium sulfate and concentrated en vacuo. The residue was purified by flash chromatography on silica eluted with 4:1 hexane/acetone to give 1.632 g (64.7%) of 4-(2-hydroxyethyl)benzoic acid methyl ester 71 as a clear oil.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for an additional 2 hours
  3. temperatureThe reaction was cooled to 0° C.
  4. customquenched with alkaline hydrogen peroxide
  5. extractionThe mixture was then extracted with diethyl ether
  6. dry with materialThe extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated en vacuo
  8. customThe residue was purified by flash chromatography on silica
  9. washeluted with 4:1 hexane/acetone

Sources & evidence

ORD record
ord-230f361beabd44599aabf26aca89ed2d
Source dataset
uspto-grants-2007_12
Patent number
US07312230B2

Reaction notes

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