Acetic Acid → HCID 21398245, compound

HRID 1439154Notes

Reaction equation

HRID 1439154 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].[CH2:19]([S:37][CH2:38][CH:39]([OH:42])CO)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].[CH3:43][O-:44].[Na+].[C:46]([OH:49])(=O)[CH3:47]>>[CH2:19]([S:37][CH2:38][CH:39]([O:42][C:43](=[O:44])[CH2:4][CH2:3][C:2]1[CH:1]=[C:47]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:46]([OH:49])=[C:12]([CH3:11])[CH:13]=1)[CH2:10][O:9][C:7](=[O:8])[CH2:6][CH2:5][C:4]1[CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]([OH:14])=[C:2]([CH3:1])[CH:3]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 165455Benzenepropanoic acid, 3-(1,1-dimethylethyl)-4-hydroxy-5-methyl-, methyl esterHCID 2459623-octadecylsulfanylpropane-1,2-diolHCID 10942334Sodium Methoxide

Product 1

HCID 21398245HCID 21398245, compound

Conditions

Temperature
80 °C

Procedure

A mixture of 15.2 grams (0.06 mole) of methyl 3-methyl-5-tert-butyl-4-hydroxyhydrocinnamate and 10.14 grams (0.027 mole) of 1-n-octadecylthio-2,3-propanediol was heated to about 80° C and stirred until the mixture became homogenous. Sodium methylate (0.292 grams, 0.0054 mole) was added, and the resulting mixture was heated at 125°-145° C for 5 hours at atmospheric pressure and another 3 hours at 135°-145° C at 0.5-5 mm. The reaction mixture was then cooled and the catalyst neutralized with 0.5 grams (0.008 mole) of glacial acetic acid. Purification of the crude product was achieved by first removing the bulk (1.0 g) of the unreacted starting ester under high vacuum in a Hickman molecular still, followed by chromatography from silica gel using benzene as the eluting solvent.

Workup

  1. temperaturethe resulting mixture was heated at 125°-145° C for 5 hours at atmospheric pressure and another 3 hours at 135°-145° C at 0.5-5 mm
  2. temperatureThe reaction mixture was then cooled
  3. customPurification of the crude product
  4. customby first removing the bulk (1.0 g) of the

Sources & evidence

ORD record
ord-bac46b3b3f004a439a39d6e08104fc3e
Source dataset
uspto-grants-1977_11
Patent number
US04058502

Reaction notes

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