Sodium Hydroxide → Muconic Acid

HRID 437494Notes

Reaction equation

HRID 437494 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][CH:5](OC)[CH:6](OC)[CH2:7][C:8]([O:10]C)=[O:9].[OH-].[Na+]>O>[C:8]([OH:10])(=[O:9])/[CH:7]=[CH:6]/[CH:5]=[CH:4]/[C:3]([OH:16])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 516972HCID 516972, compound

Product 1

HCID 5356793Muconic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

23.5 Grams (0.1 mole) of β, β'-dimethoxy-adipic acid-dimethylester were boiled under reflux with a solution of 32 g of NaOH in 50 ml of water for 8 hours, were cooled, suction-filtered, dissolved in water, were precipitated with concentrated hydrochloric acid at a pH value of 1, were washed with water until neutral and dried. 12.2 Grams (86 % of the theoretical yield) of trans, trans-muconic acid were obtained which had a melting point of from 298° to 300° C.

Workup

  1. temperaturewere cooled
  2. filtrationsuction-filtered
  3. dissolutiondissolved in water
  4. customwere precipitated with concentrated hydrochloric acid at a pH value of 1
  5. washwere washed with water until neutral and
  6. customdried
  7. custom12.2 Grams (86 % of the theoretical yield) of trans

Sources & evidence

ORD record
ord-3d39c8de26b54c7cb6772d1e78bae670
Source dataset
uspto-grants-1977_06
Patent number
US04031136

Reaction notes

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