5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl chloride → Methyl 2-hydroxy-4-[3-oxo-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate

HRID 840441Notes

Reaction equation

HRID 840441 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](Cl)=[O:15])[CH:5]=[CH:4][C:3]1=2.[OH:18][C:19]1[CH:28]=[C:27]([C:29]#[C:30][Si](C)(C)C)[CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22]>>[OH:18][C:19]1[CH:28]=[C:27]([C:29]#[C:30][C:14](=[O:15])[C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH3:17])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=3[CH:7]=2)[CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22]

Participants

3

Reactant 2

HCID 27954665,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl chlorideHCID 22641103Methyl 2-hydroxy-4-trimethylsilylethynylbenzoate

Product 1

HCID 15285826Methyl 2-hydroxy-4-[3-oxo-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate

Procedure

Following the basic procedure of Example 1(b), by reacting 2.4 g (0.01 mol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoyl chloride with 2.5 g (0.01 mol) of methyl 2-hydroxy-4-trimethylsilylethynylbenzoate, 2.9 g (74%) of the expected ester, with a melting point of 189°-190° C., were recovered.

Workup

  1. customwith a melting point of 189°-190° C., were recovered

Sources & evidence

ORD record
ord-af6a56f828f94f8683392c9a8aac7232
Source dataset
uspto-grants-2002_04
Patent number
US06368608B1

Reaction notes

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