Hydrochloric Acid → 5-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-benzoic acid

HRID 584011노트

반응식

HRID 584011 반응식
[Cl:1][C:2]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[C:15]([Cl:22])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:13][CH3:14])=[C:9]([CH:12]=1)[CH:10]=[O:11].CC(=CC)C.Cl([O-])=[O:29].[Na+].Cl>C1COCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)(C)(C)C>[Cl:1][C:2]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[C:15]([Cl:22])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:13][CH3:14])=[C:9]([CH:12]=1)[C:10]([OH:29])=[O:11]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 223448635-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-benzaldehydeHCID 23668197Sodium Chlorite

생성물 1

HCID 223449015-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-benzoic acid수율 98.4%

시약·촉매·용매 3

HCID 6386tert-Butanol용매HCID 8028Tetrahydrofuran용매HCID 62657Potassium Phosphate, Tribasic용매

실험 절차

To a solution of 5-(2,6-dichloro-4-nitro-phenoxy)-2-methoxy-benzaldehyde (3.0 g, 8.8 mmol) in a mixture of THF (50 ml), tert-butyl alcohol (50 ml) and 2-methyl-2-butene (11 ml, 132 mmol) was added dropwise a solution of sodium chlorite (7.1 g, 79 mmol) in potassium phosphate buffer (100 ml of a 0.6 M solution, 60 mmol). The resulting mixture was stirred vigorously for 16 h at RT then acidified with 1 M HCl (200 ml). The resulting mixture was extracted with EtOAC (3×150 ml). The combined EtOAc extracts were washed with 1 M HCl (2×250 ml), water (250 ml), 10% NaHSO3, and brine (250 ml). The extracts were dried (Na2SO4), filtered, and concentrated to give the title compound of Step B (3.1 g) as a yellow solid. The title product of Step B was used in the next step without further purification. MS (ES−) Calc.: 357.0. Found: 356.0 (M−1).

후처리

  1. extractionThe resulting mixture was extracted with EtOAC (3×150 ml)
  2. washThe combined EtOAc extracts were washed with 1 M HCl (2×250 ml), water (250 ml), 10% NaHSO3, and brine (250 ml)
  3. dry with materialThe extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-71477a6ff73849e5a0def288f7812721
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06924310B2

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