Ethanol → 5-(2,2,3-Trimethylcyclopent-3-en-1-yl)-pentan-2-ol

HRID 972173노트

반응식

HRID 972173 반응식
[CH3:1][CH:2]([OH:6])[CH:3]=[CH:4][CH3:5].[CH:7](O)=[CH:8][CH2:9][CH2:10][CH3:11].[CH2:13](O)[CH2:14]CCC.[H][H].[CH2:21](O)C>[Pd]>[CH3:11][C:10]1([CH3:21])[C:13]([CH3:14])=[CH:7][CH2:8][CH:9]1[CH2:5][CH2:4][CH2:3][CH:2]([OH:6])[CH3:1]

참가 물질

6

반응물 4

HCID 702EthanolHCID 15289(+-)-3-Penten-2-olHCID 86735115Pentenol pentanolHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 212172375-(2,2,3-Trimethylcyclopent-3-en-1-yl)-pentan-2-ol수율 77.7%

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

A mixture of 0.6 g of 5% palladium on carbon, 44.1 g (0.15 moles of the pent-3-en-2-ol) of the above pentenol/pentanol mixture and 50 ml of ethanol was hydrogenated at 25°-45° C and 35-52 psi until hydrogen uptake ceased. The mixture was filtered to remove the catalyst and the solvent was removed from the filtrate by distillation. The residual oil was fractionally distilled to yield 5-(2,2,3-trimethylcyclopent-3-en-1-yl)-pentan-2-ol 30.1 g (77.7% yield); bp 105-108° C (1.5 mm); mol wt. 196 (ms); ir, 3350 (s, broad), 3040 and 797 cm-1 ; nmr, 0.5δ, 0.8, 0.9 and 1.0 (6H, 4s, geminal dimethyl groups of various diastereomers in the mixture), 1.2 (3H, d, J~6 Hz, carbinol methyl), 1.3-1.5 (7H, broad complex), 1.6 (3H, broad s, olefinic methyl), 1.7-2.4 (3H, broad complex containing 1H exchangeable with D2O), 3.8 (1H, broad multiplet, carbinyl H), 5.2 (1H, broad multiplet, olefinic H).

후처리

  1. customwas hydrogenated at 25°-45° C
  2. filtrationThe mixture was filtered
  3. customto remove the catalyst
  4. customthe solvent was removed from the filtrate by distillation
  5. distillationThe residual oil was fractionally distilled

출처 및 근거

ORD 기록
ord-1729ba4644a74729bfb68a7289f9da8b
출처 데이터셋
uspto-grants-1977_10
특허 번호
US04052341

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