alpha-Ethynyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenemethanol → Methyl 2-chloro-4-(3-hydroxy-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl)benzoate

HRID 840489Notes

Reaction equation

HRID 840489 reaction equation
[C:1]([CH:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:11]([CH3:16])([CH3:15])[CH2:10][CH2:9][C:8]([CH3:18])([CH3:17])[C:7]=2[CH:6]=1)[OH:4])#[CH:2].[Cl:19][C:20]1[CH:29]=[C:28](I)[CH:27]=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23]>>[Cl:19][C:20]1[CH:29]=[C:28]([C:2]#[C:1][CH:3]([OH:4])[C:5]2[CH:14]=[CH:13][C:12]3[C:11]([CH3:16])([CH3:15])[CH2:10][CH2:9][C:8]([CH3:18])([CH3:17])[C:7]=3[CH:6]=2)[CH:27]=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23]

Participants

3

Reactant 2

HCID 11817362alpha-Ethynyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenemethanolHCID 22619433Methyl 2-chloro-4-iodobenzoate

Product 1

HCID 22619426Methyl 2-chloro-4-(3-hydroxy-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl)benzoateYield 83%

Procedure

Following the basic procedure of Example 11(d), by reacting 1.2 g (5 mmol) of α-ethynyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenemethanol with 1.6 g (5 mmol) of methyl 2-chloro-4-iodobenzoate, 1.7 g (83%) of the expected ester was obtained in the form of a brown oil.

Sources & evidence

ORD record
ord-150c78e0714b4ea784896227a58eb533
Source dataset
uspto-grants-2002_04
Patent number
US06368608B1

Reaction notes

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