HCID 14839563, compound → HCID 14839564, compound

HRID 2249319Notes

Reaction equation

HRID 2249319 reaction equation
Br[O-:2].[Na+].[C:4]([C:7]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]2[C:13]([CH3:20])([CH3:19])[CH2:12][CH2:11][C:10]([CH3:22])([CH3:21])[C:9]=2[C:8]=1[O:23][CH3:24])(=[O:6])C>O1CCOCC1.O>[CH3:24][O:23][C:8]1[C:9]2[C:10]([CH3:22])([CH3:21])[CH2:11][CH2:12][C:13]([CH3:20])([CH3:19])[C:14]=2[C:15]([O:17][CH3:18])=[CH:16][C:7]=1[C:4]([OH:6])=[O:2]

Participants

5

Reactant 2

HCID 14839563HCID 14839563, compoundHCID 23673712Sodium hypobromite

Product 1

HCID 14839564HCID 14839564, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

In a second stage, this hypobromite solution is slowly added to a stirred solution, cooled to about 5° C., of 43 g of 2-acetyl-1,4-dimethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro naphthalene, obtained in stage (b) above, in 500 cm3 of dioxane. The rate of introduction is such that the temperature does not exceed 15° C. The reaction mixture is then left to stand overnight, diluted with 300 cm3 of water, then, at a temperature lower than 20° C., the excess sodium hypobromite is destroyed by the slow addition of a 25% aqueous solution of sodium bisulfite. The expected acid is then precipitated by acidifying the mixture by the addition of 380 cm3 of 6N HCl. The precipitate is filtered, washed with water and dried under reduced pressure. 40.8 g of 1,4-dimethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalene carboxylic acid are obtained in the form of a white solid having a melting point of 187° C.

Workup

  1. customdoes not exceed 15° C
  2. waitThe reaction mixture is then left
  3. customat a temperature lower than 20° C., the excess sodium hypobromite is destroyed by the slow addition of a 25% aqueous solution of sodium bisulfite
  4. customThe expected acid is then precipitated
  5. additionby the addition of 380 cm3 of 6N HCl
  6. filtrationThe precipitate is filtered
  7. washwashed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-740b4c4e42fa418ea1fee4dc1fd20d22
Source dataset
uspto-grants-1991_08
Patent number
US05043482

Reaction notes

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