Sulfuric Acid → 1-(4-Ethoxyphenyl)cyclopropane-1-carbaldehyde

HRID 986407Notes

Reaction equation

HRID 986407 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([C:13]1([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[CH:18][CH:17]=2)[CH2:15][CH2:14]1)#N.[OH:25]S(O)(=O)=O>C1C=CC=CC=1.CCCCCCC>[CH2:23]([O:22][C:19]1[CH:20]=[CH:21][C:16]([C:13]2([CH:11]=[O:25])[CH2:15][CH2:14]2)=[CH:17][CH:18]=1)[CH3:24]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 135372511-(4-Ethoxyphenyl)cyclopropanecarbonitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 135372521-(4-Ethoxyphenyl)cyclopropane-1-carbaldehyde

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8900HeptaneSolvent

Procedure

1M Diisobutylaluminium hydride (14 ml) is added over 3 min. to a stirred solution of 1-cyano-1-(4-ethoxyphenyl)-cyclopropane (1.4 g) in dry benzene (35 ml) and dry n-heptane (14 ml) at 25° C. under an atmosphere of nitrogen. After 3 h the mixture is poured onto 2N H2SO4 (100 ml), extracted with diethyl ether (x3), dried and the solvent removed under reduced pressure. Yield 1 g, nD 1.5272.

Workup

  1. extractionextracted with diethyl ether (x3)
  2. customdried
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-0352e050f0454b80ad441eb201861bb0
Source dataset
uspto-grants-1987_12
Patent number
US04713392

Reaction notes

Loading…