Hydrochloric Acid → 3-(3-(Hydroxymethyl)phenyl)propan-1-ol

HRID 1049417Notes

Reaction equation

HRID 1049417 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10](O)=[O:11])C.O1CCCC1.B.Cl.O>C1COCC1>[OH:11][CH2:10][C:9]1[CH:8]=[C:7]([CH2:6][CH2:5][CH2:4][OH:3])[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723981Borane;tetrahydrofuran2×HCID 299280143-(3-Ethoxy-3-oxopropyl)benzoic acid

Product 1

HCID 552676803-(3-(Hydroxymethyl)phenyl)propan-1-olYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Under a nitrogen atmosphere, to a solution of 3-(3-ethoxy-3-oxopropyl)benzoic acid (2.99 g) in THF (100 mL) was added a 1.0 M solution of tetrahydrofuran-borane in tetrahydrofuran (26.9 mL) at 0° C., and the mixture was stirred in an ice bath for 18 hr. A 1.0 M solution of tetrahydrofuran-borane in tetrahydrofuran (20.0 mL) was added at 0° C., and the mixture was further stirred for 20 hr in an ice bath. 1N Hydrochloric acid (100 mL) and water were added at 0° C., and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.80 g) as a colorless oil.

Workup

  1. stirringthe mixture was further stirred for 20 hr in an ice bath
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7ce4202c1569455dafaf42b5c3a900bd
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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