Triethanolamine → Ethyl 6-hydroxy-4-methylhexa-2,4-dienoate

HRID 1719107Notes

Reaction equation

HRID 1719107 reaction equation
C([O:4][CH2:5][CH:6]=[C:7]([CH3:15])[CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=O)C.C(=O)([O-])[O-].[Na+].[Na+].N(CCO)(CCO)CCO.C(OCC)(=O)C>C(O)C>[OH:4][CH2:5][CH:6]=[C:7]([CH3:15])[CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 7618TriethanolamineHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 54268690Ethyl 6-(acetyloxy)-4-methylhexa-2,4-dienoate

Product 1

HCID 54238884Ethyl 6-hydroxy-4-methylhexa-2,4-dienoateYield 71.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

27.5 g of ethyl 6-acetoxy-4-methyl-2,4-hexadienoate, 20 g of sodium carbonate and 2 ml of triethanolamine were heated to reflux for 3 hours in 250 ml of ethanol. After the addition of ethyl acetate, the organic phase was washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated. Distillation at 110° C./0.4 mmHg gave 15.7 g (71%) of ethyl 6-hydroxy-4-methyl-2,4-hexadienoate.

Workup

  1. washthe organic phase was washed with saturated sodium chloride solution
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated
  4. distillationDistillation at 110° C./0.4 mmHg

Sources & evidence

ORD record
ord-ea7b9da8a510461684ede7de40d5d547
Source dataset
uspto-grants-1985_09
Patent number
US04539154

Reaction notes

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