Dichloromethane → 2-[3-(Quinolin-2-ylmethoxy)-benzyloxy]-6-trifluoromethyl-benzoic acid

HRID 892178Notes

Reaction equation

HRID 892178 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:30]=[CH:31][CH:32]=1)[CH2:16][O:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[C:19]=1[CH:20]=[O:21].O.O.P([O-])(O)(O)=[O:36].[Na+].Cl([O-])=O.[Na+].ClCCl>CC(=CC)C.C(O)(C)(C)C.O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:30]=[CH:31][CH:32]=1)[CH2:16][O:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[C:19]=1[C:20]([OH:36])=[O:21]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 222415012-[3-(Quinolin-2-ylmethoxy)-benzyloxy]-6-trifluoromethyl-benzaldehydeHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, Dihydrate

Product 1

HCID 222414922-[3-(Quinolin-2-ylmethoxy)-benzyloxy]-6-trifluoromethyl-benzoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolventHCID 105532-Methyl-2-buteneSolvent

Procedure

A solution of 2-[3-(quinolin-2-ylmethoxy)-benzyloxy]-6-trifluoromethyl-benzaldehyde (46 mg, 0.1 mmol, example 50) in 2-methyl-2-butene (1 mL), t-butanol (2 mL) and water (2 mL) is treated with sodium dihydrogenphosphate dihydrate (153 mg, 1.1 mmol) and sodium chlorite (198 mg, 2.2 mmol). After 45 min. the reaction is partioned between dichloromethane (50 mL) and water (50 mL). The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo to provide the title compound: m.p. 184–185° C.; 1H NMR (300 MHz, CDCl3) δ 8.28 (d, 1H), 8.12 (d, 1H), 7.82–7.75 (m, 2H), 7.66–7.55 (m, 2H), 7.42 (dd, 1H), 7.30–7.27 (m, 2H), 7.16 (d, 1H), 7.07 (dd, 1H), 6.88 (d, 1H), 6.77 (dd, 1H), 5.44 (s, 2H), 5.07 (s, 2H); MS (ESI) 454 (M+H)+.

Workup

  1. dry with materialThe organic layer is dried over magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-22ed4f6c85714ba78629595b57015f4f
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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