2-Propenoic acid, 3-(4-formylphenyl)- → (E)-4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-ethynyl]-cinnamic acid

HRID 893753Notes

Reaction equation

HRID 893753 reaction equation
Cl[CH:2](P(=O)(OCC)OCC)[C:3]1[CH:12]=[CH:11][C:10]2[C:9]([CH3:14])([CH3:13])[CH2:8][CH2:7][C:6]([CH3:16])([CH3:15])[C:5]=2[CH:4]=1.[CH:25]([C:27]1[CH:37]=[CH:36][C:30]([CH:31]=[CH:32][C:33]([OH:35])=[O:34])=[CH:29][CH:28]=1)=O>C(O)C>[CH3:13][C:9]1([CH3:14])[CH2:8][CH2:7][C:6]([CH3:16])([CH3:15])[C:5]2[CH:4]=[C:3]([C:2]#[C:25][C:27]3[CH:37]=[CH:36][C:30](/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34])=[CH:29][CH:28]=3)[CH:12]=[CH:11][C:10]1=2

Participants

4

Reactant 2

HCID 980772-Propenoic acid, 3-(4-formylphenyl)-HCID 13604831Diethyl 1-chloro-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)methylphosphonate

Product 1

HCID 19786981(E)-4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-ethynyl]-cinnamic acidYield 39.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using a procedure similar to that described in Example 6b, 16.5 g (44 millimoles) of diethyl 1-chloro-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-methylphosphonate (about 85% strength), 7.8 g (44 millimoles) of 4-formylcinnamic acid and 15.5 g (137 millimoles) of potassium tert.-butylate were converted to 6.2 g (39%) of the title compound of melting point 256°-258° C. (from ethanol).

Sources & evidence

ORD record
ord-a75f88959742469191ee892c2c57c735
Source dataset
uspto-grants-1992_06
Patent number
US05126371

Reaction notes

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