Hydrochloric Acid → HCID 13604819, compound

HRID 2292314Notes

Reaction equation

HRID 2292314 reaction equation
[C:1]([C:3]1[CH:17]=[CH:16][C:6]([CH2:7]P(=O)(OCC)OCC)=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].[CH:20]([C:22]1[C:31]([CH3:32])=[CH:30][C:29]2[C:28]([CH3:34])([CH3:33])[CH2:27][CH2:26][C:25]([CH3:36])([CH3:35])[C:24]=2[C:23]=1[O:37][CH3:38])=O.Cl>CS(C)=O.O>[CH3:38][O:37][C:23]1[C:24]2[C:25]([CH3:35])([CH3:36])[CH2:26][CH2:27][C:28]([CH3:34])([CH3:33])[C:29]=2[CH:30]=[C:31]([CH3:32])[C:22]=1/[CH:20]=[CH:7]/[C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 1747662-Naphthalenecarboxaldehyde, 5,6,7,8-tetrahydro-1-methoxy-3,5,5,8,8-pentamethyl-HCID 241438Diethyl (4-Cyanobenzyl)phosphonate

Product 1

HCID 13604819HCID 13604819, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent3×HCID 962WaterSolvent

Procedure

A solution of 25.2 g (0.1 mole) of diethyl 4-cyanobenzylphosphonate in 50 ml of dimethyl sulfoxide was added dropwise to a suspension of 3 g (0.1 mole) of sodium hydride (80% strength, freed beforehand from the 20% of paraffin using petroleum ether) in 100 ml of absolute dimethyl sulfoxide at from 25° to 40° C. The mixture was stirred for a further hour, after which a solution of 12 g (50 millimoles) of 2-formyl-5,6,7,8-tetrahydro-1-methoxy-3,5,5,8,8-pentamethylnaphthalene in 100 ml of dimethyl sulfoxide was added dropwise, and the mixture was stirred overnight at room temperature. Thereafter, the reaction mixture was poured onto 1.2 l of water and acidified with 2N hydrochloric acid, the resulting oily product was separated off and stirred with a little methanol, the crystals obtained were filtered off and the solid was washed on the filter with methanol and dried to give 13.8 g of the title compound of melting point 120° C.

Workup

  1. customat from 25° to 40° C
  2. stirringthe mixture was stirred overnight at room temperature
  3. customthe resulting oily product was separated off
  4. stirringstirred with a little methanol
  5. customthe crystals obtained
  6. filtrationwere filtered off
  7. washthe solid was washed on the
  8. filtrationfilter with methanol
  9. customdried

Sources & evidence

ORD record
ord-45b0acb7e48147ad93213d3326cd8b27
Source dataset
uspto-grants-1989_01
Patent number
US04801733

Reaction notes

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