Acetaldehyde → 2-((5-Methyl-2-(1-methylethyl)cyclohexyl)oxy)acetic acid

HRID 1110139ノート

反応式

HRID 1110139 の反応式
C(=[O:3])C.[CH3:4][CH:5]1[CH2:10][CH:9]([O:11][CH2:12][C:13](Cl)=[O:14])[CH:8]([CH:16]([CH3:18])[CH3:17])[CH2:7][CH2:6]1.CO>N1C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:4][CH:5]1[CH2:10][CH:9]([O:11][CH2:12][C:13]([OH:3])=[O:14])[CH:8]([CH:16]([CH3:18])[CH3:17])[CH2:7][CH2:6]1

参加物

7

反応物 3

HCID 177AcetaldehydeHCID 887MethanolHCID 556978HCID 556978、化合物

生成物 1

HCID 978142-((5-Methyl-2-(1-methylethyl)cyclohexyl)oxy)acetic acid

試薬・触媒・溶媒 3

HCID 1049Pyridine触媒HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

Vinyl L-menthoxyacetate is prepared from acetaldehyde, L-menthoxyacetyl chloride, and pyridine catalyst. A 70 mL stainless steel high pressure reactor fitted with a Pyrex glass liner and magnetic stir bar is charged with THF (5 mL), (PPh3)2PdCl2 (0.05 mmol), CH3OH (0.5 mmol), and vinyl L-menthoxyacetate (0.5 mmol). The reactor is sealed, pressurized to 1000 psig with CO, and stirred for 24 hours at 100° C. The product mixture, isolated after removal of gas from the reactor vessel, contains a diastereomeric mixture of methyl L-menthoxyacetyl-L-lactate and methyl L-menthoxyacetyl-D-lactate. The diastereomers are separated by preparative gas chromatography using an SE-30 liquid phase column. Each diastereomer is hydrolyzed separately by treatment with 2N HCl (aq) for 2 hours at 100° C. to give pure L- and D-lactic acid, methanol, and L-menthoxyacetic acid. The L-menthoxyacetic acid is recycled to L-menthoxyacetyl chloride by treatment with thionyl chloride.

後処理

  1. customA 70 mL stainless steel high pressure reactor fitted with a Pyrex glass liner and magnetic stir bar
  2. customThe reactor is sealed
  3. customThe product mixture, isolated
  4. customafter removal of gas from the reactor vessel
  5. additiona diastereomeric mixture of methyl L-menthoxyacetyl-L-lactate and methyl L-menthoxyacetyl-D-lactate
  6. customThe diastereomers are separated by preparative gas chromatography
  7. waitEach diastereomer is hydrolyzed separately by treatment with 2N HCl (aq) for 2 hours at 100° C.

出典と根拠

ORDレコード
ord-db6de64750e04ff08fa0fe09a4da321e
出典データセット
uspto-grants-1994_06
特許番号
US05324856

反応ノート

読み込み中…