Hydrochloric Acid → HCID 13633544, compound

HRID 980325Notes

Reaction equation

HRID 980325 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.Cl.[C:36](OC(=O)C)(=[O:38])[CH3:37].C([O-])(=O)C.[Na+]>C(O)(=O)C.[Cl-].[Zn+2].[Cl-].C(OCC)(=O)C.O>[C:36]([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:38])[CH3:37]

Participants

9

Reactant 4

HCID 313Hydrochloric Acid2×HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 13633545HCID 13633545, compound

Product 1

HCID 13633544HCID 13633544, compoundYield 92.5%

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product (5 g) obtained in Example 1, acetic acid (20 cc) and anhydrous zinc chloride (320 mg) are introduced, under an argon atmosphere, into a reactor. A solution (5 cc) of hydrochloric acid in acetic acid, containing 1.9 moles of hydrochloric acid per liter, is added. Thereafter, acetic anhydride (2.7 cc) is added over the course of 15 minutes. The temperature rises from 20° to 30° C. After 2 hours' stirring, water (10 cc), sodium acetate (800 mg) and ethyl acetate (100 cc) are added. After evaporation of the solvents, the residue is taken up in methylene chloride. After filtration over silica gel, 2,5,7,8-tetramethyl-2-(4',8',12'-trichloro-4',8',12'-trimethyl-tridecyl)-chroman-6-ol acetate (4.99 g) is obtained.

Workup

  1. additionis added
  2. customrises from 20° to 30° C
  3. customAfter evaporation of the solvents
  4. filtrationAfter filtration over silica gel

Sources & evidence

ORD record
ord-7326777b3d4d48af87a6991dca7a86e3
Source dataset
uspto-grants-1987_01
Patent number
US04636570

Reaction notes

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