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Hydrochloric Acid → Sorbitol stearate

HRID 46602
Notes
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Reaction equation

HRID 46602 reaction equation
[C:1](Cl)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH:21][CH2:22][C@@H:23]([C@H:25]([C@@H:27]([C@@H:29]([CH2:31][OH:32])[OH:30])[OH:28])[OH:26])[OH:24].Cl>C1(C)C=CC=CC=1.N1C=CC=CC=1>[C:1]([OH:19])(=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH:32][CH2:31][C@@H:29]([C@H:27]([C@@H:25]([C@@H:23]([CH2:22][OH:21])[OH:24])[OH:26])[OH:28])[OH:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5780SorbitolHCID 8212Stearoyl chloride

Product 1

HCID 86736698Sorbitol stearate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

411.5 g (1.358 mols) stearic acid chloride are dissolved in 3 l toluene and heated to 90° C. 41.23 g (0.22 mols) of sorbitol, dissolved in 200 ml pyridine are added dropwise to this mixture over 25 minutes. The solution is boiled (at approx. 110° C.) for 1 hour under reflux. After cooling, dilute hydrochloric acid is added to acidify the mixture, which is then washed with water until neutral and dried with dehydrated sodium sulphate. After concentration of the organic phase the sorbitol stearate crystallizes. It is recrystallized from methanol.

Workup

  1. additionare added dropwise to this mixture over 25 minutes
  2. custom(at approx. 110° C.)
  3. customfor 1 hour
  4. temperatureunder reflux
  5. temperatureAfter cooling
  6. washis then washed with water until neutral and
  7. dry with materialdried with dehydrated sodium sulphate
  8. customAfter concentration of the organic phase the sorbitol stearate crystallizes
  9. customIt is recrystallized from methanol

Sources & evidence

ORD record
ord-d1dca84c9b584950b7b5fa1a15b7b248
Source dataset
uspto-grants-1979_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04174325

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes