Methylparaben → N-[4-(Cyclobutylmethoxy)benzoyl]glycine

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.OC1C=CC(C(OC)=O)=CC=1.C1(CO)CCC1>>[CH:4]1([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][CH2:3][CH2:1]1

Participants

Reactant 3

HCID 7456Methylparaben

HCID 78130Cyclobutylcarbinol

HCID 66812105N-[4-(2-Cyclopropylethoxy)benzoyl]glycine

Product 1

HCID 66812262N-[4-(Cyclobutylmethoxy)benzoyl]glycineYield 97%

Procedure

The same reactions as in Example 9 (9a) and (9b) were conducted using methyl 4-hydroxybenzoate (3.81 g, 25.0 mmol) and cyclobutylmethanol (2.36 mL, 25.0 mmol) to give 6.41 g of the title compound (colorless oil, yield: 97%).

Sources & evidence

ORD record: ord-3b6347393dd04806b435ff94e543f214
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143446B2

Reaction notes

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