Methyl di-t-butyl hydroxyhydrocinnamate → HCID 86741773, compound

HRID 2308895Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[CH2:22](O)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]C>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[O:19])[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]=1[OH:11])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 120 °C

Procedure

292.4 g (1 mole) of methyl β-(3,5-di-tert.-butyl-4-hydroxyphenyl)-propionate and 383.6 g (1 mole) of oleyl alcohol are initially taken in 50 ml of toluene and are heated at 120° C., so that the toluene has distilled off in the course of one hour. 2.5 g of lithium amide are then added and the methanol which is formed is distilled off at 80° C. The mixture is then heated to 120° C. and is kept at this temperature for 4 hours. The reaction is monitored by thin layer chromatography. When the reaction is complete, the reaction mixture is dissolved in 200 ml of toluene, neutralised with 12 ml of concentrated HCl and then washed with twice 200 ml of water.

Workup

distillationhas distilled off in the course of one hour
addition2.5 g of lithium amide are then added
customthe methanol which is formed
distillationis distilled off at 80° C
dissolutionthe reaction mixture is dissolved in 200 ml of toluene
washwashed with twice 200 ml of water

Sources & evidence

ORD record: ord-010cf7d17b0d462c91bfcf9fbe901556
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04691044

Reaction notes

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