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

HRID 257722

반응식

HRID 257722 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 954.8%

시약·촉매·용매 2

HCID 7044Decalin용매HCID 8058Hexane용매

실험 절차

To a suspension of 2-methyl-1,4-dihydrobenzoic acid (0.085 g, 0.05 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). The solution was heated to reflux for 19 h. 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) δ8..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, 1H), 7.22 (dd, J=8.5, 1.5 Hz, 1H), 2.64 (s, 3H).

후처리

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

출처 및 근거

ORD 기록
ord-f43c679603694864b00aac60e59cd5bb
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05264408

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