Sodium Hydroxide → 4'-Decyloxybiphenyl-4-carboxylic Acid

HRID 1196442Notes

Reaction equation

HRID 1196442 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])C.Br[O-].[Na+].[OH-].[Na+].BrBr.S(=O)(O)[O-:35].[Na+]>O1CCOCC1>[CH2:17]([O:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:35])=[CH:5][CH:6]=2)=[CH:11][CH:12]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 24408BromineHCID 19898384HCID 19898384, compoundHCID 23665763Sodium BisulfiteHCID 23673712Sodium hypobromite

Product 1

HCID 114510854'-Decyloxybiphenyl-4-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-acetyl-4'-decyloxy-1,1'-biphenyl (4.2 g, 0.012 mol) in 1,4-dioxane (20 ml), an aqueous solution of sodium hypobromite (40 ml) [freshly prepared from sodium hydroxide (7.9 g) and bromine (7.1 g)] was added dropwise at 20°-25° C., and stirring was continued for 2 h at 40° C. After cooling, sodium bisulfite was added to destroy excess sodium hypobromite and the mixture was acidified with hydrochloric acid. The resultant precipitate was filtered, washed with H2O and dried to give the title compound as a white amorphous powder; yield: 3.5 g (90.1%); mp 245.5°-250.0° C.

Workup

  1. additionwas added dropwise at 20°-25° C.
  2. temperatureAfter cooling
  3. customto destroy excess sodium hypobromite
  4. filtrationThe resultant precipitate was filtered
  5. washwashed with H2O
  6. customdried

Sources & evidence

ORD record
ord-184b70d4307f4dbda47f08dc9f96f63c
Source dataset
uspto-grants-1992_05
Patent number
US05114615

Reaction notes

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