Ketene → HCID 178425354, compound

HRID 1673169Notes

Reaction equation

HRID 1673169 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([CH:14]3[CH2:19][CH2:18][CH:17]([CH:20]=[O:21])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:22]=[C:23]=[O:24]>C(OCC)(=O)C.[Fe](Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:9][CH2:10][C@H:11]([CH:14]3[CH2:19][CH2:18][CH:17]([CH:20]4[O:21][C:23](=[O:24])[CH2:22]4)[CH2:16][CH2:15]3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 10038Ketene3×HCID 178425355HCID 178425355, compound

Product 1

HCID 178425354HCID 178425354, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 24458Ferrous ChlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-(trans-4-(4-methylphenyl)cyclohexyl)cyclohexane-carbaldehyde (20.6 g, 72 mmol, ratio of trans-4-(trans-4-(4-methylphenyl)cyclohexyl)cyclohexanecarbaldehyde/cis-4-(trans-4-(4-methylphenyl)cyclohexyl)-cyclohexylcarbaldehyde=98/2) was dissolved in ethyl acetate (380 g), and iron chloride (FeCl3, 0.2 g, 1.2 mmol) was added thereto. 3.7 equivalents of ketene was introduced into the solution at 40° C. over 150 minutes. After completing the introduction of ketene, nitrogen was introduced for 30 minutes to eliminate the unreacted ketene. The resulting solution was concentrated to provide 4-(4-(trans-4-(4-methylphenyl)-cyclohexyl)cyclohexyl)-2-oxetanone (ratio of 4-(trans-4-(trans-4-(4-methylphenyl)cyclohexyl)cyclohexyl)-2-ox etanone/4-(cis-4-(trans-4-(4-methylphenyl)cyclohexyl)-cyclohexyl)-2-oxetanone=98/2) (27.8 g, 64 mmol, yield: 88%)).

Workup

  1. additionwas introduced for 30 minutes
  2. concentrationThe resulting solution was concentrated

Sources & evidence

ORD record
ord-638a86119d72463cbbcef51eb1fff876
Source dataset
uspto-grants-2011_08
Patent number
US07999123B2

Reaction notes

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