2'-Hydroxyacetophenone → Cyclododec-2-en-1-ol

HRID 2308173Notes

Reaction equation

HRID 2308173 reaction equation
[OH-].[Ca+2].[OH-].O[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=[O:13])[CH3:12]>>[CH:11]1([OH:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:5][CH2:7][CH2:6][CH2:5][CH:10]=[CH:12]1

Participants

3

Reactant 2

HCID 83752'-HydroxyacetophenoneHCID 6093208Calcium Hydroxide

Product 1

HCID 53886827Cyclododec-2-en-1-ol

Conditions

Temperature
215 °C

Procedure

A mixture of 180 parts of trans-1,2-epoxidodecane, 6 parts of calcium hydroxide and 0.3 parts of o-hydroxyacetophenone was refluxed at 210-220° C. for 3 hours in a three-necked flask equipped agitator, Dean-Stark trap, and temperature probe. After cooling and filtration 175 parts of the mixture containing 15% starting epoxide and 74% cyclododec-2-en-1-ol (85% conversion, 87% selectivity) was obtained.

Workup

  1. customequipped agitator, Dean-Stark trap, and temperature probe
  2. temperatureAfter cooling
  3. filtrationfiltration 175 parts of the mixture
  4. additioncontaining 15%

Sources & evidence

ORD record
ord-91497092c4104addbea1feeab9a36f7a
Source dataset
uspto-grants-2004_12
Patent number
US06835686B2

Reaction notes

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