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

HRID 257722

反応式

HRID 257722 の反応式
[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]

参加物

5

反応物 2

HCID 5645811,4-Dihydro-2-methylbenzoic acidHCID 178527255HCID 178527255、化合物

生成物 1

HCID 83732-Methylbenzoic acid収率 954.8%

試薬・触媒・溶媒 2

HCID 7044Decalin溶媒HCID 8058Hexane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f43c679603694864b00aac60e59cd5bb
出典データセット
uspto-grants-1993_11
特許番号
US05264408

関連ノート

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