Reaction SMILES: CC1C(C([C:18]2[CH:27]=[CH:26][C:21]([C:22](=[N:24][OH:25])[OH:23])=[CH:20][CH:19]=2)=O)=CC2C(C)(C)CCC(C)(C)C=2C=1.[H-].[Na+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[NH4+].[Cl-].Cl>C1COCC1.CN1C(=O)N(C)CCC1>[CH2:30]([O:25][N:24]=[C:22]([OH:23])[C:21]1[CH:20]=[CH:19][CH:18]=[CH:27][CH:26]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1
Reactant: Cc1cc2c(cc1C(=O)c1ccc(C(O)=NO)cc1)C(C)(C)CCC2(C)C
Reactant: BrCc1ccccc1
Agent: Cl
Agent: [Cl-]
Agent: [H-]
Solvent: C1CCOC1
Solvent: CN1CCCN(C)C1=O
Product: OC(=NOCc1ccccc1)c1ccccc1
Temperature: 25 °C
Reaction time: 0.5 h
Yield: 251 %

Procedure:
4-[(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl]benzoic acid (4.41 g, 12.6 mmol) in EtOH (10 mL) and pyridine (15.3 mL) was treated with hydroxylamine hydrochloride (4.38 g, 63 mmol), and the mixture was heated at reflux. After 6 h, the mixture was cooled to room temperature and the ethanol was removed in vacuo. The residue was taken-up in water and the aqueous layer was adjusted to pH=4.5 with 1 M aqueous HCl. The aqueous solution was extracted with EtOAc, 3×. The organic layer were combined and washed with water (2×) and brine. The organic solution was dried (NaSO4), filtered, and concentrated. Recrystallization (CH2Cl2/hexanes) gave 4-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl]benzoic acid oximate 4.05 g (88%) as a white solid: mp 204-209° C. (d); 1H NMR (CDCl3/d-4MeOH) δ7.99 (½ABq, J=8.4 Hz, 2H, ArH), 7.53 (½ABq, J=8.4 Hz, 2H, ArH), 7.20 (s, 1H, ArH), 6.99 (s, 1H, ArH), 2.11 (s, 3H, CH3), 1.69 (s, 4H, 2CH2), 1.32 (s, 6H, 2CH3), 1.22 (s, 6H, 2CH3); HRMS: 366.2060 (MH+). A solution of 4-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl]benzoic acid oxime (100 mg, 0.27 mmol) in THF (0.3 mL) and DMPU (0.3 mL) was added at 0° C. to a suspension of NaH (20 mg, 0.82 mmol) in THF (1.0 mL). The suspension was allowed to warm to room temperature was stirring over 30 minutes, then a solution of benzyl bromide (71 mL, 0.82 mmol) was added. The solution was allowed to warm to room temperature and stirred for 12 h. Aqueous, saturated NH4Cl (5.0 mL) was added and the aqueous layer was adjusted to pH=4-5 with 1 M aqueous HCl. The aqueous solution was extracted with EtOAc, 3×. The organic layers were combined and washed with water (2×) and brine. The organic solution was dried (Na2SO4), filtered, and concentrated to give a white solid. Purification by radial chromatography (10:1=hexanes: EtOAc) gave 4-[3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)carbonyl]benzoic acid O-benzyloxime (105) 154 mg (61%) as a white solid: mp 169-172° C.; IR (neat) 2961 m, 2926 m 1691 s, 1420 w, 1285 w, 1016 w cm−1; 1H NMR (400 MHz, CDCl3) δ8.03 (½ABq, J=8.5 Hz, 2H, ArH), 7.55 (½ABq, J=8.5 Hz, 2H, ArH), 7.31 (m, 5H, ArH), 7.15 (s, 1H, ArH), 6.96 (s, 1H, ArH), 5.25 (s, 2H, OCH2) 2.00 (s, 3H, Ar—CH3), 1.69 (s, 4H, 2CH2), 1.31 (s, 6H, 2CH3), 1.22 (s, 6H, 2CH3); 13C NMR (100.8 MHz, CDCl3) δ171.7, 156.6, 145.3, 142.2, 141.4, 138.2, 132.5, 130.2, 130.1, 129.4, 128.2, 128.1, 127.9, 127.6, 127.0, 126.2, 35.2, 35.1, 34.1, 33.9, 31.9, 19.4; MS (FAB) m/e 4.56 (MH+); HRMS (FAB, MH+) Calcd for C30H33NO3: 456.2539 Found: 456.2526.