Hydrochloric Acid → HCID 20533589, compound

HRID 1277468Notes

Reaction equation

HRID 1277468 reaction equation
CC#C.[Mg].C(Br)CBr.[O:9]([C:16]1[CH:23]=[CH:22][C:19](C=O)=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl.[O:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>>[C:27]([CH:26]([OH:25])[C:22]1[CH:19]=[CH:18][CH:17]=[C:16]([O:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:23]=1)#[C:28][CH3:29]

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 6335PropyneHCID 78391,2-DibromoethaneHCID 8028Tetrahydrofuran3×HCID 661394-PhenoxybenzaldehydeHCID 5462224Magnesium

Product 1

HCID 20533589HCID 20533589, compound

Procedure

To a solution of 8 g of methyl acetylene in 100 ml of tetrahydrofurane is slowly added at 0° C. a Grignard solution freshly prepared from 4 gof magnesium and 20 g of ethylene bromide in 20 ml of tetrahydrofurane. Themixture is stirred for 15 minutes under argon and a solution of 27 g of p-phenoxybenzaldehyde in 100 ml of tetrahydrofurane is added dropwise at 0° to 5° C. After stirring for 14 hours at room temperature,the reaction mixture is cooled to 0° C. with 50 g of ice and, after the slow addition of 25 ml of conc. hydrochloric acid, extracted with ether. The ethereal extract is washed twice with water and twice with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The product is chromatographed over silica gel with ethyl acetate/hexane (1:4) as eluant, affording the compound of the formula ##STR4##with a refractive index of nD20° =1.5898.

Workup

  1. stirringAfter stirring for 14 hours at room temperature
  2. extractionextracted with ether
  3. extractionThe ethereal extract
  4. washis washed twice with water and twice with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product is chromatographed over silica gel with ethyl acetate/hexane (1:4) as eluant
  9. customaffording the compound of the formula ##STR4##with a refractive index of nD20° =1.5898

Sources & evidence

ORD record
ord-b16faf1c59444dea9259f1549c671bed
Source dataset
uspto-grants-1981_07
Patent number
US04277494

Reaction notes

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