Methylparaben → Methyl 4-(benzyloxy)benzoate

HRID 429765

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+]>>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:6][C:5]2[CH:10]=[CH:11][CH:2]=[CH:3][CH:4]=2)=[CH:11][CH:10]=1

Participants

Reactant 2

HCID 7456Methylparaben

HCID 24758Sodium hydride

Product 1

HCID 299810Methyl 4-(benzyloxy)benzoateYield 175.7%

Procedure

The title compound (26.6 g, 110%) was prepared from methyl 4-hydroxybenzoate (15.2 g, 125 mmol) utilising sodium hydride as base, in a similar manner to Intermediate 76. 1H NMR (CDCl3) δ 8.00 (2H, d, J 8.9 Hz), 7.82-7.73 (5H, br m), 6.99 (2H, d, J 8.9 Hz), 5.12 (2H, s) and 3.89 (3H, s). MS (ES) m/e 243 [M+H]+.

Sources & evidence

ORD record: ord-4b2a3c581bfa40f0b22e2037edf4b5ad
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06319922B1

Linked notes

Loading…