Ethanol → HCID 21217237, compound

HRID 972173Notes

Reaction equation

HRID 972173 reaction equation
[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]

Participants

6

Reactant 4

HCID 702EthanolHCID 15289(+-)-3-Penten-2-olHCID 86735115HCID 86735115, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21217237HCID 21217237, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1729ba4644a74729bfb68a7289f9da8b
Source dataset
uspto-grants-1977_10
Patent number
US04052341

Reaction notes

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