Sodium Hydroxide → HCID 54438686, compound

HRID 2049704Notes

Reaction equation

HRID 2049704 reaction equation
[OH:1][C:2]([CH3:20])([C:9]([CH3:19])=[CH:10][CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][C:4]([O:6]CC)=[O:5].[OH-].[Na+].[Br:23]Br>CO.C(=O)([O-])O.[Na+].O.CO>[OH:1][C:2]1([CH3:20])[C:9]([CH3:19])([Br:23])[CH:10]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:6][C:4](=[O:5])[CH2:3]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 53696458HCID 53696458, compound

Product 1

HCID 54438686HCID 54438686, compoundYield 34.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 516892Sodium BicarbonateSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

The carboxylic acid (1.09 g) prepared by hydrolyzing 12.20 g of ethyl 3-hydroxy-3,4-dimethyl-7-phenyl-4,6-heptadienoate with 4N sodium hydroxide solution in 60 ml of methanol, was dissolved in a solution of 700 mg of sodium hydrogen carbonate in 40 ml of a solvent mixture of water-methanol (1:1) and a solution of 1.06 g of bromine in 1 ml of methanol was dropwise added thereto under cooling at -30°~-35° C. After stirring for 30 minutes, the crystals produced were collected by filtration, washed with water, dried, and recrystallized from a mixture of n-hexane and ethyl acetate (5:1) to give 750 mg of the desired compound melting at 121°-123° C.

Workup

  1. temperatureunder cooling at -30°~-35° C
  2. customthe crystals produced
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customdried
  6. customrecrystallized from a mixture of n-hexane and ethyl acetate (5:1)

Sources & evidence

ORD record
ord-2b81e433c7c4484393668ed261f35f8c
Source dataset
uspto-grants-1980_04
Patent number
US04198425

Reaction notes

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