4-((5,6,7,8-Tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoic acid → 4-[(5-Acetoxy-7,8-dihydro-8,8-dimethylnaphth-2-yl)ethynyl]benzoic acid
Reaction equation
[C:1]([O:4][C:5]1[C:6]2[CH:7]=[CH:8][C:9]([C:17]#[C:18][C:19]3[CH:29]=[CH:28][C:22]([C:23]([O:25]CC)=[O:24])=[CH:21][CH:20]=3)=[CH:10][C:11]=2[C:12]([CH3:16])([CH3:15])[CH2:13][CH:14]=1)(=[O:3])[CH3:2].CC1(C)C2C=C(C#CC3C=CC(C(O)=O)=CC=3)C=CC=2C(=O)CC1>>[C:1]([O:4][C:5]1[C:6]2[CH:7]=[CH:8][C:9]([C:17]#[C:18][C:19]3[CH:29]=[CH:28][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=3)=[CH:10][C:11]=2[C:12]([CH3:16])([CH3:15])[CH2:13][CH:14]=1)(=[O:3])[CH3:2]Participants
3
Procedure
Employing the same general procedure as for the preparation of ethyl 4-[(5-acetoxy-7,8-dihydro-8,8-dimethylnaphth-2-yl)ethynyl]benzoate (Compound 105), 274 mg (0.86 mmol) of 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonapth-2-yl)ethynyl]benzoic acid (Compound 7) was converted into the title compound (light yellow solid) using 0.22 ml (2.58 mmol) acetic anhydride and 84 mg (0.43 mmol) of p-toluenesulfonic acid.
Sources & evidence
- ORD record
- ord-59d48c1ede9d40b9b411790f659161cb
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05618931
Reaction notes
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