Formaldehyde → 2,2,3-Trimethyl-alpha-methylene-3-cyclopentene-1-acetaldehyde

HRID 1377434노트

반응식

HRID 1377434 반응식
[OH-].[Na+].C=O.[CH3:5]CCCCC.[CH3:11][C:12]1[C:16]([CH3:18])([CH3:17])[CH:15]([CH2:19][CH:20]=[O:21])[CH2:14][CH:13]=1>CO.O>[CH3:18][C:16]1([CH3:17])[C:12]([CH3:11])=[CH:13][CH2:14][CH:15]1[C:19](=[CH2:5])[CH:20]=[O:21]

참가 물질

7

반응물 4

HCID 712FormaldehydeHCID 8058HexaneHCID 14798Sodium HydroxideHCID 984973-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl-

생성물 1

HCID 202354022,2,3-Trimethyl-alpha-methylene-3-cyclopentene-1-acetaldehyde수율 215.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

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온도
0 °C

실험 절차

A 3 liter 3 neck round bottomed flask was charged with 50 g of sodium hydroxide (1.25 moles) in 250 g of methanol. 200 g of paraformaldehyde, 500 g of hexane and 2.5 g of BHA were added and the flask was cooled to 0° C. With fast agitation 500 g of campholenic aldehyde at a purity of 88.9% (2.92 moles) were added dropwise over 70 minutes keeping the temperature at 0°-5° C. The batch was stirred for 3 hours at 0° C. Then 50 ml of water was added and the layers are separated. The water layer was back extracted with 250 ml of hexane. The hexane extracts were combined and washed with 2×500 ml of 10% sodium hydroxide and 3×500 ml of water. The batch was dried and afforded 1163 g of crude 2-(2,2,3-trimethylcyclopent-3-en-1-yl)propenal in hexane. A second batch was prepared analogously affording 1169 g of crude product.

후처리

  1. customat 0°-5° C
  2. customthe layers are separated
  3. extractionThe water layer was back extracted with 250 ml of hexane
  4. washwashed with 2×500 ml of 10% sodium hydroxide and 3×500 ml of water
  5. customThe batch was dried

출처 및 근거

ORD 기록
ord-ff6e6567146a41b18082fdf0e2afd122
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665696

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