Hydrochloric Acid → 4-[3-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)propa-1,2-dienyl]benzoic acid

HRID 1003646Notes

Reaction equation

HRID 1003646 reaction equation
[CH3:1][C:2]1([CH3:28])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH2:14][C:15]#[C:16][C:17]3[CH:27]=[CH:26][C:20]([C:21]([O:23]CC)=[O:22])=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2.CO.[OH-].[Na+].Cl>O.CCCCCCC.C1COCC1>[CH3:1][C:2]1([CH3:28])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([CH:14]=[C:15]=[CH:16][C:17]3[CH:27]=[CH:26][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 18357924Ethyl 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate

Product 1

HCID 183578924-[3-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)propa-1,2-dienyl]benzoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Procedure

6.02 g (16 mmol) of ethyl 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate, 5 ml of methanol, 5 ml of THF and 50 ml of heptane are introduced into a round-bottomed flask. 850 mg of sodium hydroxide are added and the mixture is refluxed for one hour. The reaction medium is poured into water, adjusted to pH 1 with hydrochloric acid and extracted with ethyl acetate, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is triturated from ethyl alcohol, filtered and dried. 1.37 g (24.5%) of 4-[3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)propa-1,2-dienyl]benzoic acid are collected, with a melting point of 227-8° C.

Workup

  1. temperaturethe mixture is refluxed for one hour
  2. extractionextracted with ethyl acetate
  3. customthe organic phase is separated out after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue obtained
  7. customis triturated from ethyl alcohol
  8. filtrationfiltered
  9. customdried
  10. custom1.37 g (24.5%) of 4-[3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)propa-1,2-dienyl]benzoic acid are collected, with a melting point of 227-8° C.

Sources & evidence

ORD record
ord-216d963f6f344acdb819b18427734153
Source dataset
uspto-grants-2000_04
Patent number
US06046220

Reaction notes

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