Water → Beta-Carotene

HRID 2081817Notes

Reaction equation

HRID 2081817 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.C[O-].[K+].O>C1(C)C=CC=CC=1>[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

5

Reactant 3

HCID 962WaterHCID 23664618Potassium methoxideHCID 53638311HCID 53638311, compound

Product 1

HCID 5280489Beta-CaroteneYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 50-ml round-bottom flask 2.01 g (purity: 40.9%, 1.15 mmoles) 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 1.0 g (purity: 80%, 11 mmoles) of potassium methoxide in 4 g of toluene at 30° C. for 2 hours. Then water was added to the reaction mixture. The resulting organic layer was separated and washed with water, followed by removal of the solvent, to give 2.58 g (purity: 19.1%, 0.918 mmole, yield: 80%) of a-crude β-carotene. To this product 10 g of water was added. The mixture was heat-refluxed for 10 hours and subjected to extraction with toluene to remove organic substances, followed by recrystallization of the residue from toluene-methanol solvent, to give 44 mg of a dark brown crystal. The crystal thus obtained was confirmed to be β-carotene by comparison with standard sample.

Workup

  1. customThe resulting organic layer was separated
  2. washwashed with water
  3. customfollowed by removal of the solvent

Sources & evidence

ORD record
ord-911466026c274f828685f0087adf9cb6
Source dataset
uspto-grants-1993_02
Patent number
US05185468

Reaction notes

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