Linalool → 2-Methyl-3-buten-2-ol
Reaction equation
[CH2:1]=[CH:2][C:3]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])([CH3:5])[OH:4].C(OC)(=O)[CH2:13][C:14]([CH3:16])=[O:15].[CH3:20][C:21]([OH:25])([CH3:24])[CH:22]=[CH2:23].CC([O-])C.CC([O-])C.CC([O-])C.[Al+3]>>[CH2:1]([CH2:13][C:14](=[O:15])[CH3:16])/[CH:2]=[C:3](/[CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])\[CH3:5].[CH3:10][C:9](=[CH:8][CH2:7][CH2:6][C:3](=[O:4])[CH3:2])[CH3:11].[CH3:20][C:21]([OH:25])([CH3:24])[CH:22]=[CH2:23]Participants
Conditions
- Temperature
- 165 °C
Procedure
A mixture of 637 g of linalool (91% pure), 36 g of methyl acetoacetate, 6 g of 3-methyl-but-1-en-3-ol and 8.6 g of aluminum isopropylate was heated to 165° C. in the apparatus described in Example 12, and 642 g of methyl acetoacetate and 211 g of 3-methyl-but-1-en-3-ol were added dropwise in the course of 10 hours whilst maintaining a reaction temperature of 165° C., the temperature at the 2nd theoretical plate being kept at about 100° C. After a further 4 hours' reaction time at 165° C., the mixture was worked up by distillation. 681 g of geranylacetone, 212 g of 2-methyl-hept-2-en-6-one and 37 g of unconverted 3-methyl-but-1-en-3-ol were obtained. The selectivities achieved are accordingly as follows: 87% based on 3-methyl-but-1-en-3-ol, 94%, based on linalool, and 88%, based on methyl acetoacetate.
Workup
- additionwere added dropwise in the course of 10 hours
- temperaturewhilst maintaining a reaction temperature of 165° C.
- custombeing kept at about 100° C
- customAfter a further 4 hours' reaction time at 165° C.
- distillationthe mixture was worked up by distillation
Sources & evidence
- ORD record
- ord-dd40096dcadc499ea0ced13881c75567
- Source dataset
- uspto-grants-1982_01
- Patent number
- US04310705
Reaction notes
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