Ethyl bromoacetate → 2-Methoxy-6-isopropylphenoxyacetic Acid

HRID 967012ノート

反応式

HRID 967012 の反応式
Br[CH2:2][C:3]([O:5]CC)=[O:4].[OH-].[Na+].[CH:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:14]=1[OH:21])([CH3:12])[CH3:11]>C1(C)C=CC=CC=1.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[CH3:20][O:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH:10]([CH3:12])[CH3:11])[C:14]=1[O:21][CH2:2][C:3]([OH:5])=[O:4]

参加物

7

反応物 3

HCID 7748Ethyl bromoacetate2 回HCID 14798Sodium HydroxideHCID 125212842-Methoxy-6-(propan-2-yl)phenol

生成物 1

HCID 105133162-Methoxy-6-isopropylphenoxyacetic Acid収率 72%

試薬・触媒・溶媒 3

HCID 66133Benzyl triethylammonium chloride触媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒3 回

実験手順

A solution of 11.1 ml of ethyl bromoacetate in 10 ml of toluene was added dropwise at room temperature over about 15 minutes into a mixture of 20 g of NaOH, 30 ml of H2O, 1.1 g of triethylbenzylammonium chloride, 8.4 g of 2-isopropyl-6-methoxyphenol (prepared according to Johnson et al., Tetrahedron. 38, 1397-1404 (1982)) and 40 ml of toluene. The mixture was stirred vigorously at the same temperature for 2 h and thereafter for 2 h at 60-65° C. and for 6.5 h under reflux. During this last step a solution of 6 ml of ethyl bromoacetate in 10 ml of toluene was added. In the end the mixture was diluted with 250 ml of H2O. The aqueous phase was separated off and treated with concentrated HCl; the emulsified precipitate was extracted with Et2O (3×50 ml) and the organic phase was washed with water. Another extraction was performed with 40 ml of 20% Na2CO3 and the slightly alkaline solution was treated with concentrated HCl and extracted with Et2O (3×40 ml). The extracts were pooled and the solvent was evaporated off, giving 8 g (72%) of the desired compound; b.p. 190° C./0.7 mmHg.

後処理

  1. waitfor 2 h at 60-65° C.
  2. temperaturefor 6.5 h under reflux
  3. customThe aqueous phase was separated off
  4. additiontreated with concentrated HCl
  5. extractionthe emulsified precipitate was extracted with Et2O (3×50 ml)
  6. washthe organic phase was washed with water
  7. extractionAnother extraction
  8. additionthe slightly alkaline solution was treated with concentrated HCl
  9. extractionextracted with Et2O (3×40 ml)
  10. customthe solvent was evaporated off

出典と根拠

ORDレコード
ord-960af535151542ae9883fe7adefa1fe0
出典データセット
uspto-grants-2005_10
特許番号
US06953800B2

反応ノート

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