Hydrochloric Acid → 3-m-Anisyl-1-propanol

HRID 2290935Notes

Reaction equation

HRID 2290935 reaction equation
[CH3:1][O:2][C:3]1[CH2:4][CH:5]([CH:11]=[CH:12][CH:13]=1)[CH:6]=[CH:7][C:8](O)=[O:9].B.C1COCC1.Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][CH2:8][OH:9])[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 54574549HCID 54574549, compound

Product 1

HCID 961303-m-Anisyl-1-propanolYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of dihydro-m-methoxycinnamic acid (90 g, 0.5 mole) and tetrahydrofuran (250 mL) was stirred under N2 at 0° as BH3.THF (1M solution, 525 mL) was added slowly. The reaction mixture was stirred at room temperature for 2 hours. After cooling to -5° C., 1N HCl was added. THF was evaporated and water was added to the residue. The aqueous layer was extracted with ether. The combined extracts were washed with saturated aqueous NaHCO3, saturated aqueous NaCl, dried (MgSO4), filtered and evaporated to yield 70.0 g white solid, M+ 166.

Workup

  1. additionwas added slowly
  2. temperatureAfter cooling to -5° C.
  3. customTHF was evaporated
  4. additionwater was added to the residue
  5. extractionThe aqueous layer was extracted with ether
  6. washThe combined extracts were washed with saturated aqueous NaHCO3, saturated aqueous NaCl
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-7e56279a166a461288a45e806106795f
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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