Allyl bromide → 1,3,5-Trimethyl-phenyl allyl ether
Reaction equation
[CH3:1][C:2]1([OH:10])[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[CH2:3]1.[CH2:11](Br)[CH:12]=[CH2:13]>>[CH2:13]([O:10][C:2]1([CH3:1])[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH2:7]1)[CH:12]=[CH2:11]Participants
Procedure
The 5-(4-allyloxy-2,3,6-trimethyl-phenyl)-3-methyl-penta-2,4-diene-1-triphenylphosphonium bromide employed as the starting material can be prepared by the procedure of Example 3. This procedure is carried out by alkylation of 1,3,5-trimethylphenol with allyl bromide to give 1,3,5-trimethyl-phenyl allyl ether (boiling point 76°-80° C./0.05 mmHg), by formylation of the ether obtained to give 4-allyloxy-2,3,6-trimethyl-benzaldehyde (boiling point 90°-102° C./0.15 mmHg), by condensation of the aldehyde obtained with acetone to give 4-(4-allyloxy-2,3,6-trimethyl-phenyl)-but-3-en-1-al (boiling point 135°-138° C./0.05 mmHg), by reaction of the ketone obtained with acetylene to give 5-(4-allyloxy-2,3,6-trimethyl-phenyl)-3-methyl-3-hydroxy-penta-4-en-1-yne, by partial hydrogenation of the tertiary acetylene carbinol obtained to give 5-(4-allyloxy-2,3,6-trimethyl-phenyl)-3-methyl-3-hydroxy-penta-1,4-diene and by reaction of the tertiary ethylene carbinol obtained with triphenylphosphine hydrobromide. There is obtained 5-(4-allyloxy-2,3,6-trimethyl-phenyl)-3-methyl-penta-2,4-diene-triphenylphosphonium bromide which melts at 114°-116° C.
Workup
- customcan be prepared by the procedure of Example 3
Sources & evidence
- ORD record
- ord-d133a5e56255439fa9cae0dcd5e4d1f8
- Source dataset
- uspto-grants-1985_07
- Patent number
- US04532355
Reaction notes
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