p-Toluenesulfonic acid → 1-(2-Tetrahydropyranyl)oxy-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraene
Reaction equation
[CH3:1][C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:21])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:20])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])=[CH:3][CH2:4][OH:5].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:33]1[CH:38]=[CH:37][CH2:36][CH2:35][CH2:34]1>C(Cl)Cl>[O:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]1[O:5][CH2:4][CH:3]=[C:2]([CH3:1])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:21])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:20])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18]Participants
5
Procedure
In methylene chloride were dissolved 15 g of 3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen-1-ol and 1.5 g of p-toluenesulfonic acid, and to the solution was dropwise added, under stirring, 8.7 g of 2,3-dihydropyran, at 0°-5° C. and over a period of 30 min. The resulting solution was further stirred at 0°-5° C. for 30 min., and then washed with an aqueous sodium carbonate solution in a separatory funnel. The solution was concentrated after the washing, and the concentrated solution was purified over a silica gel column to give 13 g of 1-(2-tetrahydropyranyl)oxy-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraene (yield 68%).
Workup
- additionto the solution was dropwise added
- stirringThe resulting solution was further stirred at 0°-5° C. for 30 min.
- washwashed with an aqueous sodium carbonate solution in a separatory funnel
- concentrationThe solution was concentrated after the washing
- customthe concentrated solution was purified over a silica gel column
Sources & evidence
- ORD record
- ord-3a75a36321744d4199b5ff6ac949748e
- Source dataset
- uspto-grants-1982_07
- Patent number
- US04338251
Reaction notes
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