Water → Beta-Carotene

HRID 2254913Notes

Reaction equation

HRID 2254913 reaction equation
C1(S([CH:10]([C:42]2[C:47]([CH3:49])([CH3:48])[CH2:46][CH2:45][CH2:44][C:43]=2[CH3:50])[CH:11]=[C:12]([CH3:41])[CH:13](Cl)[CH2:14][CH2:15][C:16]([CH3:39])=[CH:17][CH:18]=[CH:19][CH:20]=[C:21]([CH3:38])[CH:22]=[CH:23][CH:24]=[C:25]([CH3:37])[CH:26]=[CH:27][C:28]2[C:33]([CH3:35])([CH3:34])[CH2:32][CH2:31][CH2:30][C:29]=2[CH3:36])(=O)=O)C=CC=CC=1.[OH-].[K+].O.C1(C)C=CC=CC=1>C(O)C>[CH3:50][C:43]1[CH2:44][CH2:45][CH2:46][C:47]([CH3:48])([CH3:49])[C:42]=1/[CH:10]=[CH:11]/[C:12](/[CH3:41])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:39])=[CH:17]/[CH:18]=[CH:19]/[CH:20]=[C:21](\[CH3:38])/[CH:22]=[CH:23]/[CH:24]=[C:25](\[CH3:37])/[CH:26]=[CH:27]/[C:28]1[C:33]([CH3:35])([CH3:34])[CH2:32][CH2:31][CH2:30][C:29]=1[CH3:36]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 14797Potassium HydroxideHCID 53638311HCID 53638311, compound

Product 1

HCID 5280489Beta-CaroteneYield 81.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 50-ml round-bottom flask 1.32 g (purity: 40.9%, 0.76 mmole) of 1-phenylsulfonyl-4-chloro-1,18-di(2,6,6-trimethyl-1-cyclohexen-1-yl)-3,7,12,16-tetramethyloctadeca-2,7,9,11,13,15,17-heptaene was reacted with 0.8 g (purity: 85%, 12.1 mmoles) of potassium hydroxide in 15 g of ethanol at 45° C. for 3 hours. Then water and toluene were added and the reaction mixture was separated. The organic layer obtained was washed with water and the solvent was removed therefrom to obtain 1.95 g (purity: 17.2%, 0.62 mmole, yield: 81.6%) of β-carotene.

Workup

  1. customthe reaction mixture was separated
  2. customThe organic layer obtained
  3. washwas washed with water
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-20013cebc243462fb17f6f2788c11f3c
Source dataset
uspto-grants-1993_08
Patent number
US05237102

Reaction notes

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