Methylparaben → N-[4-(3-Cyclopropylpropoxy)benzoyl]glycine

HRID 1099560Notes

Reaction equation

HRID 1099560 reaction equation
[CH:1]1([CH2:4][CH2:5][O:6][C:7]2[CH:19]=[CH:18][C:10]([C:11]([NH:13][CH2:14][C:15]([OH:17])=[O:16])=[O:12])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.O[C:21]1C=CC(C(OC)=O)=CC=1.C1(CCCO)CC1>>[CH:3]1([CH2:1][CH2:4][CH2:5][O:6][C:7]2[CH:8]=[CH:9][C:10]([C:11]([NH:13][CH2:14][C:15]([OH:17])=[O:16])=[O:12])=[CH:18][CH:19]=2)[CH2:2][CH2:21]1

Participants

4

Reactant 3

HCID 7456MethylparabenHCID 204264853-Cyclopropylpropan-1-olHCID 66812105N-[4-(2-Cyclopropylethoxy)benzoyl]glycine

Product 1

HCID 66812145N-[4-(3-Cyclopropylpropoxy)benzoyl]glycineYield 51%

Procedure

The same reactions as in Example 9 (9a) and (9b) were conducted using methyl 4-hydroxybenzoate (6.09 g, 40.0 mmol) and 3-cyclopropylpropan-1-ol (which is the compound disclosed in Helv. Chim. Acta, (2003), 86, 865-893, 4.41 g, 44.0 mmol) to give 5.74 g of the title compound (white powder, yield: 51%).

Sources & evidence

ORD record
ord-0237b2dd432d4968b0595f9189c380f1
Source dataset
uspto-grants-2012_03
Patent number
US08143446B2

Reaction notes

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