Ethanol → 1-Naphthol

HRID 1867247Notes

Reaction equation

HRID 1867247 reaction equation
[C:1]1([O:11]C2C3C(=CC=CC=3)C=CC=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br.C(O)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:7]1[CH:8]=[CH:9][C:10]2[C:5](=[CH:4][CH:3]=[CH:2][C:1]=2[OH:11])[CH:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 25134Boron tribromideHCID 2356111-Naphthyl etherHCID 516892Sodium Bicarbonate

Product 1

HCID 70051-NaphtholYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

Naphthylether 10 (19.8 g, 81 mmol) was dissolved in a dry DCM (400 mL) and the solution cooled to −70° C. A solution of BBr3 (1M in DCM, 160 mL, 160 mmol) was added dropwise while maintaining an internal temperature below −60° C. The mixture was aged at this temperature for an additional 30 min, then allowed to warm up to RT and aged for additional 2 h at rt. The mixture was then again cooled to −70° C., treated with absolute ethanol (20 mL), and the resulting mixture was aged at rt overnight. The solution was poured into a cold NaHCO3 solution (500 mL, saturated aq) and vigorously stirred. The organic layer was washed with dilute HCl solution (0.1N, 200 mL) and with water (200 mL), and the solvent removed. Column chromatography of the resulting residue using 20% ethyl acetate in hexanes yielded the naphthylester 12 (17.6 g, 76.4 mmol) in 94% yield.

Workup

  1. temperaturewhile maintaining an internal temperature below −60° C
  2. temperatureto warm up to RT
  3. waitaged for additional 2 h at rt
  4. temperatureThe mixture was then again cooled to −70° C.
  5. waitthe resulting mixture was aged at rt overnight
  6. washThe organic layer was washed with dilute HCl solution (0.1N, 200 mL) and with water (200 mL)
  7. customthe solvent removed

Sources & evidence

ORD record
ord-c6cd9d6621fc45449f88b90e427e0bc1
Source dataset
uspto-grants-2009_12
Patent number
US07632828B2

Reaction notes

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