4-(Difluoromethoxy)-3-methoxybenzaldehyde → 4-Trifluoroethoxy-3-hydroxybenzaldehyde

HRID 506493Notes

Reaction equation

HRID 506493 reaction equation
FC(F)OC1C=CC(C=O)=CC=1OC.[F:15][C:16]([F:30])([F:29])[CH2:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][C:20]=1[O:27]C>>[F:15][C:16]([F:29])([F:30])[CH2:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][C:20]=1[OH:27]

Participants

3

Reactant 2

HCID 31612494-(Difluoromethoxy)-3-methoxybenzaldehydeHCID 126474993-Methoxy-4-(2,2,2-trifluoroethoxy)benzaldehyde

Product 1

HCID 866252254-Trifluoroethoxy-3-hydroxybenzaldehydeYield 81%

Procedure

Repeating Example 3, except that 4-difluoromethoxy-3-methoxybenzaldehyde was replaced with 70 grams (0.3 mol) of 4-trifluoroethoxy-3-methoxybenzaldehyde to give 4-trifluoroethoxy-3-hydroxybenzaldehyde (m.p. 133˜135° C.) in a yield of 81%. 1H-NMR (ppm) δ: 9.81 (1H, s; —CHO); 7.26 (1H, m; 6-ArH); 7.17 (1H, m; 2-ArH); 6.79 (1H, m; 5-ArH); 4.88 (1H, s; —OH); 4.45 (2H, q; J3H-F=7.2 Hz; —CH2CF3). 13C-NMR (ppm)) δ: 191.0 (CHO), 157.2 (4-ArC), 146.2 (3-ArC), 130.6 (1-ArC), 126 (q, CF3), 123.5 (6-ArC), 116.7 (2-ArC), 116.2 (5-ArC), 87 (m, CH2).

Sources & evidence

ORD record
ord-2a67233422e4413da91b39fe13040fd8
Source dataset
uspto-grants-2010_08
Patent number
US07786098B2

Reaction notes

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