Carbon Dioxide → HCID 13633544, compound

HRID 978914Notes

Reaction equation

HRID 978914 reaction equation
[CH3:1][C:2]1([CH2:16][CH2:17][CH2:18][C:19]([Cl:34])([CH3:33])[CH2:20][CH2:21][CH2:22][C:23]([Cl:32])([CH3:31])[CH2:24][CH2:25][CH2:26][C:27]([Cl:30])([CH3:29])[CH3:28])[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([CH3:15])[C:6]([CH3:14])=[C:7]([OH:13])[C:8]=2[CH3:12])[O:3]1.CN(C1C=CC=CN=1)C.[C:44](OC(=O)C)(=[O:46])[CH3:45].C(=O)([O-])[O-].[Na+].[Na+].C(=O)=O>CCCCCC.O.C(N(CC)CC)C>[C:44]([O:13][C:7]1[C:8]([CH3:12])=[C:9]2[C:4](=[C:5]([CH3:15])[C:6]=1[CH3:14])[O:3][C:2]([CH3:1])([CH2:16][CH2:17][CH2:18][C:19]([Cl:34])([CH3:33])[CH2:20][CH2:21][CH2:22][C:23]([Cl:32])([CH3:31])[CH2:24][CH2:25][CH2:26][C:27]([Cl:30])([CH3:28])[CH3:29])[CH2:11][CH2:10]2)(=[O:46])[CH3:45]

Participants

9

Reactant 5

HCID 280Carbon DioxideHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 218852-DimethylaminopyridineHCID 13633545HCID 13633545, compound

Product 1

HCID 13633544HCID 13633544, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

The product obtained in Example 3 (2.1 g), dimethylaminopyridine (150 mg) and triethylamine (10 cc) are introduced, under an argon atmosphere, into a three-neck flask and acetic anhydride (6 cc) is then added rapidly, with stirring, at a temperature of 25° C. After 1 hour's stirring, water (20 cc) is added and the reaction mixture is thereafter neutralised by gradual addition of sodium carbonate until the evolution of carbon dioxide gas ceases. The reaction mixture is extracted with ethyl acetate (twice 50 cc). The organic phase is washed with a 0.1N aqueous hydrochloric acid solution (3 times 50 cc). The organic phases are dried over magnesium sulphate. After filtration and evaporation of the solvent, the residue obtained is taken up in hexane. The precipitate which forms is filtered off. This gives a 93% yield of 2,5,7,8-tetramethyl-2-(4',8',12'-trichloro-4',8',12'-trimethyl-tridecyl)-chroman-6-ol acetate, melting at 95°-105° C.

Workup

  1. stirringAfter 1 hour's stirring
  2. extractionThe reaction mixture is extracted with ethyl acetate (twice 50 cc)
  3. washThe organic phase is washed with a 0.1N aqueous hydrochloric acid solution (3 times 50 cc)
  4. dry with materialThe organic phases are dried over magnesium sulphate
  5. filtrationAfter filtration and evaporation of the solvent
  6. customthe residue obtained
  7. filtrationThe precipitate which forms is filtered off

Sources & evidence

ORD record
ord-c857822d932c4ec5a1aa06e394228246
Source dataset
uspto-grants-1987_05
Patent number
US04665244

Reaction notes

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