5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbaldehyde → (5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-(4-tolyl)-acetylene

HRID 982050Notes

Reaction equation

HRID 982050 reaction equation
Cl[CH:2](P(=O)(OCC)OCC)[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.[CH:18]([C:20]1[CH:29]=[CH:28][C:27]2[C:26]([CH3:31])([CH3:30])[CH2:25][CH2:24][C:23]([CH3:33])([CH3:32])[C:22]=2[CH:21]=1)=O>>[CH3:30][C:26]1([CH3:31])[CH2:25][CH2:24][C:23]([CH3:33])([CH3:32])[C:22]2[CH:21]=[C:20]([C:18]#[C:2][C:3]3[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=3)[CH:29]=[CH:28][C:27]1=2

Participants

3

Reactant 2

HCID 104208875,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbaldehydeHCID 13604830Diethyl [chloro(4-methylphenyl)methyl]phosphonate

Product 1

HCID 19786979(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-(4-tolyl)-acetyleneYield 56%

Procedure

Using a process similar to that described in Example 13, 61.4 g (0.22 mole) of diethyl 1-chloro-1-(4-tolyl)-methylphosphonate, 51.1 g (0.22 mole) of 2-formyl5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene and 50 g (0.44 mole) of potassium tert.-butylate were reacted for 1 hour to give 37.1 g (56%) of the title compound of melting point 99° C., the reaction mixture being poured onto water and acidified, and the precipitated solid being filtered off under suction and recrystallized twice from methanol.

Workup

  1. customwere reacted for 1 hour

Sources & evidence

ORD record
ord-c694f78e5df14fb7941ad58883d3314c
Source dataset
uspto-grants-1991_02
Patent number
US04994489

Reaction notes

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