Ethyl 4-[(7,8-dihydro-5,8,8-trimethylnaphth-3-yl)ethynyl]benzoate → 4-[(5,8,8-Trimethyl-7,8-dihydronaphth-3-yl)ethynyl]benzoic acid

HRID 2393843Notes

Reaction equation

HRID 2393843 reaction equation
[CH3:1][C:2]1([CH3:27])[C:11]2[CH:10]=[CH:9][C:8]([C:12]#[C:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)=[CH:7][C:6]=2[C:5]([C:23](C)(C)C)=[CH:4][CH2:3]1.CC1C2C=C(C#CC3C=CC(C(OCC)=O)=CC=3)C=CC=2C(C)(C)CC=1>>[CH3:23][C:5]1[C:6]2[CH:7]=[C:8]([C:12]#[C:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)[CH:9]=[CH:10][C:11]=2[C:2]([CH3:1])([CH3:27])[CH2:3][CH:4]=1

Participants

3

Reactant 2

HCID 18314561Ethyl 4-[(7,8-dihydro-5,8,8-trimethylnaphth-3-yl)ethynyl]benzoate2×HCID 183145964-[(7,8-Dihydro-8,8-dimethyl-5-(1,1-dimethylethyl)naphth-3-yl)ethynyl]benzoic acid2×

Product 1

HCID 183145894-[(5,8,8-Trimethyl-7,8-dihydronaphth-3-yl)ethynyl]benzoic acid

Procedure

Employing the same general procedure as for the preparation of 4-[(7,8-dihydro-8,8-dimethyl-5-(1,1-dimethylethyl)naphth-3-yl)ethynyl]benzoic acid (Compound 80), 33.7 mg (0.10 mmol) of ethyl 4-[(7,8-dihydro-5,8,8-trimethylnaphth-3-yl)ethynyl]benzoate (Compound 73) was converted into the title compound (colorless solid) using 10.2 mg (0.25 mmol) of LiOH in H2O.

Sources & evidence

ORD record
ord-663869c9db934463aad5a080b36609c0
Source dataset
uspto-grants-1998_09
Patent number
US05808083

Reaction notes

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