Ethyl 4-[(7,8-dihydro-5,8,8-trimethylnaphth-2-yl)ethynyl]benzoate → 4-[(7,8-Dihydro-5,8,8-trimethylnaphth-2-yl)ethynyl]benzoic acid

HRID 277546Notes

Reaction equation

HRID 277546 reaction equation
[CH3:1][C:2]1([CH3:29])[C:11]2[CH:10]=[C:9]([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:8]=[CH:7][C:6]=2[C:5]([C:23]2C=CC=CC=2)=[CH:4][CH2:3]1.CC1C2C=CC(C#CC3C=CC(C(OCC)=O)=CC=3)=CC=2C(C)(C)CC=1>>[CH3:23][C:5]1[C:6]2[CH:7]=[CH:8][C:9]([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:10][C:11]=2[C:2]([CH3:1])([CH3:29])[CH2:3][CH:4]=1

Participants

3

Reactant 2

HCID 18314553Ethyl 4-[(7,8-dihydro-5,8,8-trimethylnaphth-2-yl)ethynyl]benzoate2×HCID 183145904-[(7,8-Dihydro-8,8-dimethyl-5-phenylnaphth-2-yl)ethynyl]benzoic acid2×

Product 1

HCID 183145954-[(7,8-Dihydro-5,8,8-trimethylnaphth-2-yl)ethynyl]benzoic acid

Procedure

Employing the same general procedure as for the preparation of 4-[(7,8-dihydro-8,8-dimethyl-5-phenylnaphth-2-yl)ethynyl]benzoic acid (Compound 97), 37 mg (0.11 mmol) of ethyl 4-[(7,8-dihydro-5,8,8-trimethylnaphth-2-yl)ethynyl]benzoate (Compound 95) was converted to the title compound (white solid) using 23 mg (1.1 ml, 0.54 mmol) of LiOH (0.5 M aqueous solution).

Sources & evidence

ORD record
ord-ecc64b5948874562bfb32eeda9deb98c
Source dataset
uspto-grants-2002_03
Patent number
US06355806B1

Reaction notes

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