Nitric Acid → 7-tert-Butyl-2,3-dihydro-3,3-dimethyl-5-nitro-benzofuran

HRID 2292483노트

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HRID 2292483 반응식
[C:1]([C:5]1[C:10]2[O:11][CH2:12][C:13]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N+:16]([O-])([OH:18])=[O:17].CCCCCC>C(O)(=O)C>[C:1]([C:5]1[C:10]2[O:11][CH2:12][C:13]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([N+:16]([O-:18])=[O:17])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 944Nitric AcidHCID 8058HexaneHCID 11805831HCID 11805831, 화합물

생성물 1

HCID 107531427-tert-Butyl-2,3-dihydro-3,3-dimethyl-5-nitro-benzofuran

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
24 °C

실험 절차

A solution of 7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan (10.0 g, 49.0 mmol) in glacial acetic acid 80 mL) is treated with 70% nitric acid (4.0 mL, 63.7 mmol) dropwise, and allowed to stir at 24° C. for 4 h. TLC (hexane) is used to monitor reaction progress. The reaction mixture is partitioned between Et2O (100 mL) and H2O (100 mL). The Et2O layer is washed with H2O (50 mL) and saturated Na2 CO3 (50 mL), dried (MgSO4), filtered and evaporated to a red solid (9.12 g). Crystallization from hexane provides 7-tert-butyl-3,3-dimethyl-5-nitro-2,3-dihydrobenzo[b]furan as an orange solid.

후처리

  1. customreaction progress
  2. customThe reaction mixture is partitioned between Et2O (100 mL) and H2O (100 mL)
  3. washThe Et2O layer is washed with H2O (50 mL) and saturated Na2 CO3 (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to a red solid (9.12 g)
  7. customCrystallization from hexane

출처 및 근거

ORD 기록
ord-f6ad421a5c99424eb18fbb7e820671a8
출처 데이터셋
uspto-grants-1997_11
특허 번호
US05684002

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