Lithium Hydroxide → HCID 11708094、化合物

HRID 2253300ノート

反応式

HRID 2253300 の反応式
C([O:4][CH:5]1[CH:10]=[C:9]([CH3:11])[CH2:8][CH2:7][CH:6]1[C:12]([O:14]C)=[O:13])(=O)C.[Li+].[OH-].CCCCCC.CCOC(C)=O>O.CC(OC)(C)C.CC(O)=O>[OH:4][CH:5]1[CH:10]=[C:9]([CH3:11])[CH2:8][CH2:7][CH:6]1[C:12]([OH:14])=[O:13]

参加物

8

反応物 4

HCID 3939Lithium HydroxideHCID 8058HexaneHCID 8857Ethyl AcetateHCID 11715455Methyl 2-acetoxy-4-methylcyclohex-3-ene carboxylate

生成物 1

HCID 11708094HCID 11708094、化合物収率 72%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 15413tert-Butyl methyl ether溶媒

実験手順

A 100 mL round-bottom flask equipped with a magnetic stir bar and nitrogen inlet was charged with the acetate ester 14 (5.306 g, 25 mmol) and a solution of LiOH (8.392 g, 200 mmol) in 53 mL of H2O. The reaction was stirred for 3 h at room temperature. TLC (2:1:0.5 Hexane:EtOAc:HOAc) indicated reaction was complete. 20 mL of MTBE was added and the aqueous phase removed to a separate flask. The aqueous solution was cooled to ˜5-10° C. and acidified to pH˜2 with concentrated HCl. A small amount of precipitate was removed by filtration at room temperature. The filtrate was extracted with 3×40 mL of MTBE and the combined organic layers dried over sodium sulphate and rotovaped to a yellow oil that solidified upon cooling to give 2.798 g (72%) of the hydroxy acid 16.

後処理

  1. customA 100 mL round-bottom flask equipped with a magnetic stir bar and nitrogen inlet
  2. customreaction
  3. customthe aqueous phase removed to a separate flask
  4. temperatureThe aqueous solution was cooled to ˜5-10° C.
  5. customA small amount of precipitate was removed by filtration at room temperature
  6. extractionThe filtrate was extracted with 3×40 mL of MTBE
  7. dry with materialthe combined organic layers dried over sodium sulphate
  8. temperatureupon cooling

出典と根拠

ORDレコード
ord-bcb709557e1b4a9292d2b9d1108c72af
出典データセット
uspto-grants-2008_01
特許番号
US07323576B2

反応ノート

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