1-Butanol → HCID 178450655, compound

HRID 1742402Notes

Reaction equation

HRID 1742402 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH3:14])([CH3:13])[CH2:8][CH2:7][C:6]2([CH3:16])[CH3:15])#[CH:2].[CH:17]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)=O.[NH2:29][C:30]([NH2:32])=[O:31].S(=O)(=O)(O)O.[CH2:38](O)[CH2:39][CH2:40]C>CCOCC.O>[C:23]([C:22]1[CH:27]=[CH:28][C:19]([C:17]2[CH:2]=[C:1]([C:3]3[CH:12]=[CH:11][C:10]4[C:9]([CH3:14])([CH3:13])[CH2:8][CH2:7][C:6]([CH3:16])([CH3:15])[C:5]=4[CH:4]=3)[N:32]=[C:30]([OH:31])[N:29]=2)=[CH:20][CH:21]=1)([O:25][CH2:26][CH2:38][CH2:39][CH3:40])=[O:24]

Participants

8

Reactant 5

HCID 2631-ButanolHCID 1118Sulfuric AcidHCID 1176UreaHCID 15294Methyl 4-FormylbenzoateHCID 147265491,1,4,4-Tetramethyl-6-ethynyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 178450655HCID 178450655, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

21 g (0.1 mole) of 6-ethynyl-1,2,3,4-tetrahydro1,1,4,4-tetramethylnaphthalene, 16 g (0.1 mole) of methyl 4-formylbenzoate, 9 g (0.15 mole) of urea and 15 ml of concentrated sulfuric acid in 50 ml of n-butanol were refluxed for 4 hours. After cooling, the mixture was poured onto 500 ml of water, 100 ml of ether were added and stirring was carried out for 5 minutes. A solid was precipitated between phases. In a shaking funnel, the aqueous phase was separated off and the residue was again washed with water and then shaken thoroughly with 200 ml of petroleum ether. The precipitate was filtered off under suction and washed with petroleum ether. 6.5 g of the title compound of melting point 267°-277° C. were obtained in this manner.

Workup

  1. temperatureAfter cooling
  2. additionwere added
  3. customA solid was precipitated between phases
  4. customIn a shaking funnel, the aqueous phase was separated off
  5. washthe residue was again washed with water
  6. stirringshaken thoroughly with 200 ml of petroleum ether
  7. filtrationThe precipitate was filtered off under suction
  8. washwashed with petroleum ether

Sources & evidence

ORD record
ord-f422179cb975428b925af8e9ae01d1f1
Source dataset
uspto-grants-1994_08
Patent number
US05338749

Reaction notes

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