Sulfuric Acid → HCID 11095317, compound

HRID 1073479Notes

Reaction equation

HRID 1073479 reaction equation
CC(C[AlH]CC(C)C)C.[C:10]1([C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[C:18]#N)[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=1.C([O:26]CC)C.S(=O)(=O)(O)O>C(Cl)Cl>[C:10]1([C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[CH:18]=[O:26])[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 14487Diisobutylaluminum hydrideHCID 12856162HCID 12856162, compound

Product 1

HCID 11095317HCID 11095317, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

360 ml. (0.36 mol) 1M DIBAH solution in methylene chloride was added dropwise in the course of 1.5 hours, while cooling to -15° to -10° C., into a solution of 60.5 g. (0.33 mol) o-(1-cyclohexenyl)-benzonitrile in 500 ml. anhydrous diethyl ether, stirred for a further hour at 0° C., subsequently for 3 hours at ambient temperature and decomposed with 5N sulphuric acid. The precipitate obtained was filtered off with suction and the organic phase was washed with an aqueous solution of sodium chloride, dried and evaporated. The aldehyde obtained was used for the following stage without further purification (crude yield 95% of theory). NMR,(60 MHz, CDCl3, ppm): 10.25 (1H, s, --CHO); 6.90-8.10 (4H, m. aromat. protons); 5.70 (1H, m, olef. proton); 1.05-2.50 (8H, m, cyclohexenyl radical).

Workup

  1. temperaturewhile cooling to -15° to -10° C., into a solution of 60.5 g
  2. customThe precipitate obtained
  3. filtrationwas filtered off with suction
  4. washthe organic phase was washed with an aqueous solution of sodium chloride
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-aeeedd910e6d466db3a9d4b19ae3ff71
Source dataset
uspto-grants-1990_11
Patent number
US04970077

Reaction notes

Loading…