Phosphorus pentachloride → Tetradecan-7-one

HRID 1721833Notes

Reaction equation

HRID 1721833 reaction equation
C([C@H]1CC[C@H:7]([CH:10]2CC[C:13]3([C:32](=[O:33])[C:17]4(CC[CH:20]([C@H:23]5CC[C@H](CCC)[CH2:25][CH2:24]5)[CH2:19][CH2:18]4)C3=O)[CH2:12][CH2:11]2)[CH2:6]C1)CC.P(Cl)(Cl)(Cl)(Cl)Cl>C(Cl)(Cl)(Cl)Cl>[CH3:6][CH2:7][CH2:10][CH2:11][CH2:12][CH2:13][C:32](=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 178447817HCID 178447817, compound

Product 1

HCID 12536898Tetradecan-7-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

1 mmol of 3,11-bis(trans-4-propylcyclohexyl)dispiro-[5.1.5.1]tetradecane-7,14-dione (obtainable according to Example 1) are stirred with 210 mg (1 mmol) of phosphorus pentachloride in 30 ml of carbon tetrachloride for 48 hours at room temperature. After pouring onto ice-water, the organic phase is worked up. After chromatographic purification, 3,11-bis(trans-4-propylcyclohexyl)-14,14-dichlorodispiro[5.1.5.1.]tetradecan-7-one is obtained, m.p. 159°, c.p. 266.7°-270.1°.

Workup

  1. additionAfter pouring onto ice-water
  2. customAfter chromatographic purification, 3,11-bis(trans-4-propylcyclohexyl)-14,14-dichlorodispiro[5.1.5.1

Sources & evidence

ORD record
ord-f88cd3df191149278febc5287c9aed5f
Source dataset
uspto-grants-1989_08
Patent number
US04853151

Reaction notes

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