Naphthalen-2-yl diethylcarbamate → 2-Naphthol

HRID 1920542Notes

Reaction equation

HRID 1920542 reaction equation
C(N(CC)C(=O)[O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)C>C1COCC1>[CH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]=[CH:15][C:6]=1[OH:5]

Participants

3

Reactant 1

HCID 735640Naphthalen-2-yl diethylcarbamate

Product 1

HCID 86632-NaphtholYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of naphthalen-2-yl diethylcarbamate (73.0 mg, 0.3 mmol) and Cp2ZrCl2 (265.8 mg, 0.9 mmol, 3 eq.) in THF (4 mL) at 0° C. was added 1 M THF solution of LiAlH(Ot-Bu)3 (0.9 mL, 0.9 mmol, 3 eq.). After addition, the resultant cloudy mixture was warmed to RT and stirred for 3 hours. The reaction was quenched by H2O. The procedures outlined in Example 1a regarding acidification, extraction, and purification were performed. Naphthalen-2-ol (40.8 mg, 95% yield) was obtained as a colorless solid. Its melting point was determined to be 120-121° C. (EtOAc/hexanes). NMR (400 MHz, CDCl3) δ ppm: 7.77 (m, 2H), 7.69 (d, J=8.23 Hz, 1H), 7.44 (td, J=7.52, 0.99 Hz, 1H), 7.34 (td, J=7.51, 0.98 Hz, 1H), 7.15 (d, J=2.33 Hz, 1H), 7.11 (dd, J=8.80, 2.51 Hz, 1H), 5.06 (brs, 1H). 13C NMR (101 MHz, CDCl3) δ ppm: 153.26, 134.55, 129.84, 128.93, 127.74, 126.51, 126.34, 123.61, 117.69, 109.48. The physical and spectral data were consistent with those reported by Morley et al. (see Morley, J. A.; Woolsey, N. F., J. Org. Chem. 1992, 57, 6487-95), who reported a melting point of 121-123° C.

Workup

  1. additionAfter addition
  2. customThe reaction was quenched by H2O
  3. extractionacidification, extraction, and purification

Sources & evidence

ORD record
ord-af814617601a435e8c9db430b8b851e3
Source dataset
uspto-grants-2012_05
Patent number
US08168833B2

Reaction notes

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