Sodium Hydroxide → (E,E)-3,7,11,15-tetramethyl-6,10,14-hexadecatrienoic acid chloride
Reaction equation
[CH3:1][CH:2]([CH2:7][CH2:8]/[CH:9]=[C:10](\[CH3:22])/[CH2:11][CH2:12]/[CH:13]=[C:14](\[CH3:21])/[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])[CH2:3][C:4](O)=[O:5].[OH-].[Na+].O1C=CN=C1[Cl:30]>C1C=CC=CC=1>[CH3:1][CH:2]([CH2:7][CH2:8]/[CH:9]=[C:10](\[CH3:22])/[CH2:11][CH2:12]/[CH:13]=[C:14](\[CH3:21])/[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])[CH2:3][C:4]([Cl:30])=[O:5]Participants
5
Conditions
- Temperature
- 50 °C
Procedure
At room temperature, 9.2 g of the compound obtained in step (c) above was dropped into a 55% benzene suspension containing 1.3 g of sodium hydroxide, and the mixture was stirred at 50° C. for 10 minutes. The liquid reaction mixture was cooled to room temperature, and 3.8 g of oxazolyl chloride was dropped into the liquid reaction mixture and the resulting mixture was stirred at 50° C. for 30 minutes. The liquid reaction mixture was filtered and the solvent was removed from the filtrate by distillation under reduced pressure at a temperature lower than 40° C. to obtain 9.5 g of the intended compound in the form of an oil.
Workup
- customThe liquid reaction mixture
- temperaturewas cooled to room temperature
- stirringthe resulting mixture was stirred at 50° C. for 30 minutes
- customThe liquid reaction mixture
- filtrationwas filtered
- customthe solvent was removed from the filtrate by distillation under reduced pressure at a temperature lower than 40° C.
Sources & evidence
- ORD record
- ord-d96e2874010d4fa3b65177913fd2f079
- Source dataset
- uspto-grants-1984_06
- Patent number
- US04456603
Reaction notes
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