Aluminum isopropoxide → HCID 20454277, compound
Reaction equation
[NH:1]([C:8]1[CH:21]=[CH:20][C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](OC)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24].CC([O-])C.CC([O-])C.CC([O-])C.[Al+3].[Na]>>[C:22]([O:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:11]1[CH:20]=[CH:21][C:8]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:9][CH:10]=1)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]Participants
Conditions
- Temperature
- 88 °C
Procedure
A mixture of 6-(p-anilinophenoxy)hexanol (28.5 g.) and methyl pivalate (34.5 g.) to which 0.3 g. of aluminum isopropylate and a small chip of sodium metal had been added was heated at 88° C. while stirring for about 3 hours. Gas chromatography indicated that transesterification was not complete. Methyl pivalate was distilled from the reaction allowing the temperature to rise to 160° C. and was then added slowly back to the mixture at such a rate that the temperature could be maintained at 175°-185° C. After two hours, the reaction mixture was stripped of volatiles by heating at 120° C. under reduced pressure (150 mm of mercury). The solid residue obtained on cooling was recrystallized from 2-propanol to afford the ester, 6-(p-anilinophenoxy)hexyl pivalate as a crystalline solid, m.p. 64°-65° C.
Workup
- distillationMethyl pivalate was distilled from the reaction
- customto rise to 160° C.
- additionwas then added slowly back to the mixture at such a rate that the temperature
- temperaturecould be maintained at 175°-185° C
- waitAfter two hours
- temperatureby heating at 120° C. under reduced pressure (150 mm of mercury)
- customThe solid residue obtained
- temperatureon cooling
- customwas recrystallized from 2-propanol
Sources & evidence
- ORD record
- ord-d9b40cbb6d704c2687e43679b04205aa
- Source dataset
- uspto-grants-1979_02
- Patent number
- US04141848
Reaction notes
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