Benzene → HCID 53713151, compound
Reaction equation
[CH3:1][O:2][C:3]([CH3:19])([CH3:18])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:17])[CH2:8][CH:9]=[CH:10][C:11]([CH3:16])=[CH:12][C:13]([OH:15])=[O:14].C(Cl)(=O)C(Cl)=O.[CH:26]1[CH:31]=[CH:30][CH:29]=CC=1>>[CH:31]1([CH2:26][O:14][C:13](=[O:15])[CH:12]=[C:11]([CH3:16])[CH:10]=[CH:9][CH2:8][CH:7]([CH3:17])[CH2:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])([CH3:18])[CH3:19])[CH2:29][CH2:30]1Participants
Procedure
Under nitrogen, to a stirred solution of 3.42 g. of 11-methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid (mostly trans, trans) in dry benzene, is added 3.5 ml. of oxalyl chloride. The reaction mixture is stirred for 2 hours at room temperature and then solvent and any excess oxalyl chloride are removed in vacuo. Then about 130 ml. of fresh dry benzene is added followed by 4.46 of cyclopropylmethyl alcohol and the reaction mixture stirred, under nitrogen, overnight. The reaction is worked up by pouring into water, washing with brine, drying over calcium sulfate, removing solvent in vacuo and stirring the concentrate in pentane with neutral alumina. Pentane is removed to yield cyclopropylmethyl-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate which is purified by distillation to give a product having a boiling point of 90° (bath) at 0.01 mm.
Workup
- customsolvent and any excess oxalyl chloride are removed in vacuo
- additionof fresh dry benzene is added
- stirringthe reaction mixture stirred, under nitrogen, overnight
- additionby pouring into water
- washwashing with brine
- dry with materialdrying over calcium sulfate
- customremoving solvent in vacuo
- stirringstirring the
- concentrationconcentrate in pentane with neutral alumina
- customPentane is removed
Sources & evidence
- ORD record
- ord-ac146c6917ee49e080664b299524567f
- Source dataset
- uspto-grants-1977_02
- Patent number
- US04008258
Reaction notes
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