1,4-Dihydro-2-methylbenzoic acid → 2-Methylbenzoic acid

HRID 2396553

반응식

HRID 2396553 반응식
[CH3:1][C:2]1[CH:3]([CH:7]=[CH:8][CH2:9][CH:10]=1)[C:4]([OH:6])=[O:5]>C1C2C(CCCC2)CCC1.CCCCCC>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

참가 물질

5

반응물 2

HCID 5645811,4-Dihydro-2-methylbenzoic acidHCID 178527255HCID 178527255, 화합물

생성물 1

HCID 83732-Methylbenzoic acid수율 96%

시약·촉매·용매 2

HCID 7044Decalin용매HCID 8058Hexane용매

실험 절차

To a suspension of 2-methyl-l,4-dihydrobenzoic acid (0.085 g, 0.50 mmol; 81% pure, from Aldrich Chemical Company) in decalin (5 mL) under a nitrogen atmosphere was added the polysiloxane matrix material containing a homogeneous dispersion of metal particles (0.100 g as prepared according to Example 1). The solution was heated to reflux for 19 hours. On cooling the reaction mixture was diluted with hexane (25 mL) and extracted with aqueous sodium hydroxide (5%) solution (2×5 mL). The basic aqueous solution was acidified and extracted with chloroform (3×4 mL). The combined organic layer was dried over anhydrous sodium sulfate. Removal of solvent on rotary evaporator gave 2-methylbenzoic acid (0.065 g. 96%). IR(KBr) 3600-2000 (br), 2923, 1694, 1300, 920,731 cm-1. 1H NMR (300 MHz, CDCl3) δ 8.03 (ddd, J=8.5, 3.0, 1.5 Hz, 1 H), 7.42 (td, J=8.5, 1.5 Hz, 1H), 7.26 (td, J=8.5, 1.5 Hz, 1 H), 7.22 (dd, J=8.5, 1.5 Hz, 1 H), 2.64 (s, 3H).

후처리

  1. additioncontaining
  2. customa homogeneous dispersion of metal particles (0.100 g as prepared according to Example 1)
  3. temperatureThe solution was heated
  4. temperatureto reflux for 19 hours
  5. temperatureOn cooling the reaction mixture
  6. extractionextracted with aqueous sodium hydroxide (5%) solution (2×5 mL)
  7. extractionextracted with chloroform (3×4 mL)
  8. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  9. customRemoval of solvent
  10. customon rotary evaporator

출처 및 근거

ORD 기록
ord-3b8aca4417cf4ada848e3468cba3041f
출처 데이터셋
uspto-grants-1996_02
특허 번호
US05492964

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