Quinoline → cis-2,5-Dimethyl-3-hexene-2,5-diol

HRID 1660371Notes

Reaction equation

HRID 1660371 reaction equation
C(=O)([O-])[O-].[Ca+2].N1C2C(=CC=CC=2)C=CC=1.[CH3:16][C:17]([OH:25])([C:19]#[C:20][C:21]([CH3:24])([OH:23])[CH3:22])[CH3:18].[H][H]>CO>[CH3:16][C:17]([OH:25])(/[CH:19]=[CH:20]\[C:21]([CH3:24])([OH:23])[CH3:22])[CH3:18]

Participants

6

Reactant 4

HCID 7047QuinolineHCID 88832,5-Dimethyl-3-hexyne-2,5-diolHCID 10112Calcium CarbonateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 11126394cis-2,5-Dimethyl-3-hexene-2,5-diolYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.6 g of 5% palladized calcium carbonate and 0.6 g of quinoline were added to a solution of 24 g of 2,5-dimethyl-hex-3-yne-2,5-diol [Ray et al, Am. Soc., Vol. 74 (1952), p. 1247]in 200 ml of methanol and the mixture was stirred with hydrogen until hydrogen absorption ceased. The catalyst was removed by filtration and the filtrate was evaporated to dryness under reduced pressure to obtain 24.2 g of cis 2,5-dimethyl-hex-3-ene-2,5-diol melting at 64° C. which was used as is for the next step.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-30984089630f4520a4e0deabcbb2ad91
Source dataset
uspto-grants-1981_12
Patent number
US04307244

Reaction notes

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