Hydrochloric Acid → HCID 178439008, compound

HRID 1893081Notes

Reaction equation

HRID 1893081 reaction equation
C[O:2][CH:3]=[C:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH:18]3[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH3:26])[CH2:20][CH2:19]3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.Cl>C1COCC1>[CH2:24]([CH:21]1[CH2:20][CH2:19][CH:18]([CH2:17][CH2:16][C:13]2[CH:12]=[CH:11][C:10]([C@H:7]3[CH2:8][CH2:9][C@H:4]([CH:3]=[O:2])[CH2:5][CH2:6]3)=[CH:15][CH:14]=2)[CH2:23][CH2:22]1)[CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 584532161-[4-(Methoxymethylene)cyclohexyl]-4-[2-(4-propylcyclohexyl)ethyl]-benzene

Product 1

HCID 178439008HCID 178439008, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[4-(methoxymethylene)cyclohexyl]-4-[2-(4-propylcyclohexyl)ethyl]-benzene (1.23 g, 2.74 mmol) was refuxed by a mixture of THF and 2N HCl (10 ml) in a volume ratio of 4:1. After reaction termination, the resulting solution was diluted by distilled water (10 ml), extracted by ether extraction (5 ml×2 times), and washed by distilled water (5 ml×2 times). The residue was purified by column chromatography (ethyl acetate:petroleum ether=1:60). The ratio of cis or trans-isomer of the obtained crystal was 1:5 with NMR analysis. The crystal was performed by fractional recrystallization with hexane to obtain pure trans-4-{4-[2-(4-propylcyclohexyl)ethyl]phenyl}cyclohexane carbaldehyde (0.2 g, 18%).

Workup

  1. customAfter reaction termination
  2. additionthe resulting solution was diluted
  3. distillationby distilled water (10 ml)
  4. extractionextracted by ether extraction (5 ml×2 times)
  5. washwashed
  6. distillationby distilled water (5 ml×2 times)
  7. customThe residue was purified by column chromatography (ethyl acetate:petroleum ether=1:60)
  8. customThe crystal was performed by fractional recrystallization with hexane

Sources & evidence

ORD record
ord-f2f22b00eed34ce8bb61ac1a8266a04f
Source dataset
uspto-grants-2013_08
Patent number
US08512598B2

Reaction notes

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