Methyl 4-Iodo-3-methylbenzoate → Methyl 3-methyl-4-[3-hydroxy-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate

HRID 840488Notes

Reaction equation

HRID 840488 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].[CH3:19][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][C:29]=1I)[C:23]([O:25][CH3:26])=[O:24]>>[CH3:19][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][C:29]=1[C:2]#[C:1][CH:3]([OH:4])[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)[C:23]([O:25][CH3:26])=[O:24]

Participants

3

Reactant 2

HCID 231757Methyl 4-Iodo-3-methylbenzoateHCID 11817362alpha-Ethynyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenemethanol

Product 1

HCID 22619406Methyl 3-methyl-4-[3-hydroxy-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate

Procedure

Following the basic procedure of Example 11(d), by reacting 2.4 g (10 mmol) of α-ethynyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenemethanol with 2.7 g (10 mmol) of methyl 3-methyl-4-iodobenzoate, 3.2 g (83%) of the expected ester, with a melting point of 130°-131° C., were obtained.

Workup

  1. customwith a melting point of 130°-131° C., were obtained

Sources & evidence

ORD record
ord-c3d9da546565426681de0c753e5e4264
Source dataset
uspto-grants-2002_04
Patent number
US06368608B1

Reaction notes

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