Methyl 4-iodosalicylate → HCID 22619422, compound

HRID 861796Notes

Reaction equation

[C:1]([CH:3]([C:5]1[C:14]([O:15][CH3:16])=[CH:13][C:12]2[C:11]([CH3:18])([CH3:17])[CH2:10][CH2:9][C:8]([CH3:20])([CH3:19])[C:7]=2[CH:6]=1)[OH:4])#[CH:2].[OH:21][C:22]1[CH:31]=[C:30](I)[CH:29]=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25]>>[OH:21][C:22]1[CH:31]=[C:30]([C:2]#[C:1][CH:3]([OH:4])[C:5]2[C:14]([O:15][CH3:16])=[CH:13][C:12]3[C:11]([CH3:18])([CH3:17])[CH2:10][CH2:9][C:8]([CH3:20])([CH3:19])[C:7]=3[CH:6]=2)[CH:29]=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25]

Participants

Reactant 2

HCID 11380407Methyl 4-iodosalicylate

HCID 22619471HCID 22619471, compound

Product 1

HCID 22619422HCID 22619422, compoundYield 76.6%

Procedure

Following the basic procedure of Example 11(d), by reacting 1.15 g (4.2 mmol) of α-ethynyl-3-methoxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenemethanol with 1.21 g (4.64 mmol) of methyl 2-hydroxy-4-iodobenzoate, 1.36 g (76%) of the expected product, with a melting point of 125°-126° C., were obtained.

Sources & evidence

ORD record: ord-48dea287d6484d3dad321449e0bcd20f
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05716624

Reaction notes

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