Hydrogen Peroxide → HCID 19990526, compound

HRID 1650220Notes

Reaction equation

HRID 1650220 reaction equation
[CH2:1]([C:5]1([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]#[N:24])[CH:6]1[OH:25])[CH2:2][CH2:3][CH3:4].[OH-:30].[Na+].OO>C(O)C.C(OCC)(=O)C>[CH2:1]([C:5]1([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23](=[O:30])[NH2:24])[CH:6]1[OH:25])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 19990538HCID 19990538, compound

Product 1

HCID 19990526HCID 19990526, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2,2-dibutyl-5-(2-cyanobenzyloxy)-1,2,3,4-tetrahydro-1-naphthol (500 mg) in a mixture of ethanol (3.5 ml) and aqueous 6N-sodium hydroxide solution (0.275 ml) was added aqueous 30% hydrogen peroxide (2.62 ml) in one portion at ambient temperature. The mixture was stirred for 5 hours at 50° C. and allowed to stand overnight at ambient temperature. The reaction mixture was diluted with ethyl acetate (40 ml). The separated organic layer was washed with aqueous hydrochloric acid, aqueous sodium bicarbonate solution, and brine, and then dried, and evaporated under reduced pressure. The residue was crystallized from aqueous ethanol to yield 2,2-dibutyl-5-(2-carbamoylbenzyloxy)-1,2,3,4-tetrahydro-1-naphthol (425 mg). mp: 73°-75° C. IR (CHCl3) 3480, 3400, 2910, 1665, 1580 cm-1. NMR (CDCl3, δ): 0.86 (3H, t, J=7 Hz), 0.93 (3H, t, J=7 Hz), 1.03-1.80 (15H, m), 2.47 (1H, m), 2.76 (1H, m), 4.33 (1H, s), 5.27 (2H, s), 5.77 (1H, br s), 6.38 (1H, br s), 6.90 (1H, d, J=8 Hz), 7.03 (1H, d, J=8 Hz), 7.20 (1H, t, J=8 Hz), 7.41 (1H, t, J=8 Hz), 7.51 (1H, t, J=8 Hz), 7.62 (1H, d, J=8 Hz), 7.68 (1H, d, J=8 Hz).

Workup

  1. waitto stand overnight at ambient temperature
  2. washThe separated organic layer was washed with aqueous hydrochloric acid, aqueous sodium bicarbonate solution, and brine
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was crystallized from aqueous ethanol

Sources & evidence

ORD record
ord-a973bf3490f14ff6b53ef9a73edcc044
Source dataset
uspto-grants-1990_05
Patent number
US04923881

Reaction notes

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