Hydrogen Peroxide → HCID 19990526, compound

HRID 1089238Notes

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

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).

Workup

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

Sources & evidence

ORD record: ord-13f2e328af774beebb89c9c854ffd78a
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04965274

Reaction notes

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