3-Methylbenzyl alcohol → (3-Methylbenzyloxy)acetic Acid Ethyl Ester

HRID 18805

反応式

HRID 18805 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[N+](=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][O:6][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([CH3:1])[CH:3]=1)[CH3:17]

参加物

6

反応物 2

HCID 114763-Methylbenzyl alcoholHCID 12192Ethyl diazoacetate

生成物 1

HCID 68569289(3-Methylbenzyloxy)acetic Acid Ethyl Ester収率 101.9%

試薬・触媒・溶媒 3

HCID 423677Acetic acid, rhodium salt (4:2)触媒HCID 6344Dichloromethane溶媒HCID 8900Heptane溶媒

実験手順

To a solution of 3-methylbenzyl alcohol (1.08 g, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (0.95 mL, 9.0 mmol). The reaction mixture is stirred at RT for 30 min. The reaction mixture is diluted with heptane, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 150° C. to give 1.91 g of the product 396. 1H NMR (CDCl3) δ 7.3-7.1 (m, 4H), 4.60 (s, 2H), 4.23 (q, 2H), 4.09 (s, 2H), 2.36 (s, 3H), 1.29 (t, 311); MS: m/z 209 (M++1).

後処理

  1. filtrationfiltered through Celite
  2. customthe filtrate is evaporated
  3. distillationdistilled at 150° C.

出典と根拠

ORDレコード
ord-5290beb9104f4659ac77188b00c8bd54
出典データセット
uspto-grants-2010_06
特許番号
US07741493B2

関連ノート

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