Oxacyclohexadecane-2,13-dione → Pentadecalactone

HRID 1109252Notes

Reaction equation

HRID 1109252 reaction equation
O=[C:2]1[CH2:18][CH2:17][CH2:16][O:15][C:13](=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.N(OCCCC)=O.S(=O)(O)[O-].[Na+]>>[C:13]1(=[O:14])[O:15][CH2:16][CH2:17][CH2:18][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

3

Reactant 2

HCID 3094320Oxacyclohexadecane-2,13-dioneHCID 86747906Butyl nitrite sodium bisulphite

Product 1

HCID 235414Pentadecalactone

Procedure

The process of Russian Inventor's Certificate 521,274 is a variant in which the macrocyclic ring is retained in all the reaction steps: II is converted into 12-oxo-15-pentadecanolide (VI) using butyl nitrite/sodium bisulphite, and the product is reduced by the Clemmensen method to give 15-pentadecanolide: ##STR5## The yield of I in this process is only 36%, as can be seen from the examples. Electrochemical reduction of VI to I in accordance with German Offenlegungsschrift 3,127,242 also proceeds in only moderate yields of about 60%.

Workup

  1. customthe reaction steps

Sources & evidence

ORD record
ord-1b8b666190bb4f13a64cc99f48fb390f
Source dataset
uspto-grants-1994_06
Patent number
US05319104

Reaction notes

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