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

HRID 1110139노트

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HRID 1110139 반응식
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

참가 물질

7

반응물 3

HCID 177AcetaldehydeHCID 887MethanolHCID 556978HCID 556978, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 1049Pyridine촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
100 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-db6de64750e04ff08fa0fe09a4da321e
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05324856

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