4-((7,8-Dihydro-8,8-dimethyl-5-(1-pentynyl)naphth-3-yl)ethynyl]benzoic acid → 4-[(7,8-Dihydro-8,8-dimethyl-5-(1-propynyl)naphth-3-yl)ethynyl]benzoic acid

HRID 2393846Notes

Reaction equation

HRID 2393846 reaction equation
[CH3:1][C:2]1([CH3:28])[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:24][CH2:25]CC)=[CH:4][CH2:3]1.CC1(C)C2C=CC(C#CC3C=CC(C(OCC)=O)=CC=3)=CC=2C(C#CC)=CC1>>[CH3:1][C:2]1([CH3:28])[C:11]2[CH:10]=[CH:9][C:8]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:21][CH:22]=3)=[CH:7][C:6]=2[C:5]([C:23]#[C:24][CH3:25])=[CH:4][CH2:3]1

Participants

3

Reactant 2

HCID 183145594-((7,8-Dihydro-8,8-dimethyl-5-(1-pentynyl)naphth-3-yl)ethynyl]benzoic acid2×HCID 18314587Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(1-propynyl)naphth-3-yl)ethynyl]benzoate2×

Product 1

HCID 183145854-[(7,8-Dihydro-8,8-dimethyl-5-(1-propynyl)naphth-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-pentynyl)naphth-3-yl)ethynyl]benzoic acid (Compound 84), 75.0 mg (0.204 mmol) of ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(1-propynyl)naphth-3-yl)ethynyl]benzoate (Compound 77) was converted into the title compound (colorless solid) using 21.4 mg (0.51 mmol) of LiOH in H2O.

Sources & evidence

ORD record
ord-45551a2cc8b44bcf8ace1fb16be11291
Source dataset
uspto-grants-1998_09
Patent number
US05808083

Reaction notes

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