Dibromomethane → Methylidenecyclotridecane

HRID 1589155Notes

Reaction equation

HRID 1589155 reaction equation
[CH:1]1([CH:14]=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.BrCBr.C1(=O)CCCCCCCCCCCC1>[Ti](Cl)(Cl)(Cl)Cl.[Zn].O1CCCC1>[CH2:14]=[C:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

7

Reactant 3

HCID 3024DibromomethaneHCID 79114CyclotridecanoneHCID 20247944Cyclotridecanecarbaldehyde

Product 1

HCID 13867802Methylidenecyclotridecane

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The cyclotridecanecarbaldehyde listed above is also a novel compound which is prepared in the following manner: Titanium tetrachloride is added to a mixture of zinc dust, anhydrous tetrahydrofuran and dibromomethane. To the resulting mixture is added cyclotridecanone to yield methylene cyclotridecane which is then epoxidized with m-chloroperbenzoic acid. After purification, the epoxidized product is reacted with boron trifluoride-ether complex in anhydrous dichloromethane to yield cyclotridecanecarbaldehyde.

Workup

  1. customis prepared in the following manner

Sources & evidence

ORD record
ord-d4299876a4694bef9e6e660807ed5027
Source dataset
uspto-grants-1986_02
Patent number
US04568490

Reaction notes

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