3-Chloro-2-methyl-1-propene → HCID 15137055, compound

HRID 374859Notes

Reaction equation

HRID 374859 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl[CH2:13][C:14]([CH3:16])=[CH2:15]>>[CH3:15][C:14](=[CH2:13])[CH2:16][O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

3

Reactant 2

HCID 112413-Chloro-2-methyl-1-propeneHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 15137055HCID 15137055, compound

Procedure

Using procedures analogous to those of D. W. Robertson, et. al., J. Med. Chem., 35, 310 (1992) and V. Peesapati, and N. Lingaiah, Org. Prep. Proc. Int., 24(1), 27 (1992), the hydroxy group of methyl 3-hydroxybenzoate was alkylated with 3-chloro-2-methyl-1-propene to give methyl 3-(2-methyl-2-propenyloxy)benzoate. This material then underwent a 3,3 sigmatrophic shift to give methyl 3-hydroxy-4-(2-methyl-2-propenyl)benzoate. Formic acid catalyzed ring closure resulted in 2,2-dimethyl-6-carboxymethyl-dihydrobenzofuran.

Sources & evidence

ORD record
ord-6f05ae39ca81419c8a33a86be71524f9
Source dataset
uspto-grants-1996_01
Patent number
US05482962

Reaction notes

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