Benzyl Bromide → 4-Benzyloxy-3-ethyl-5-methylbenzaldehyde

HRID 2069397Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7]([C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([CH3:18])[C:16]=1[OH:17])[CH:12]=[O:13])[CH3:8].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH2:19]([O:17][C:16]1[C:15]([CH3:18])=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][C:9]=1[CH2:7][CH3:8])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Potassium carbonate (4.38 g, 32 mmol) is added to a stirred solution of 3-ethyl-4-hydroxy-5-methyl-benzaldehyde (2.6 g, 16 mmol) in acetone (70 mL). Benzylbromide (2.07 mL, 17 mmol) is then added dropwise and the reaction mixture is heated to 60° C. for 3 h. The suspension is filtered, the filtrate is evaporated and the crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 4-benzyloxy-3-ethyl-5-methyl-benzaldehyde (3.66 g) as a colorless oil; 1H NMR (CDCl3): δ 1.28 (t, J=7.5 Hz, 3H), 2.40 (s, 3H), 2.76 (q, J=7.5 Hz, 2H), 4.90 (s, 2H), 7.50-7.35 (m, 5H), 7.62 (s, 1H), 7.65 (s, 1H), 9.94 (s, 1H).

Workup

filtrationThe suspension is filtered
customthe filtrate is evaporated
customthe crude product is purified by CC on silica gel eluting with heptane:EA 9:1

Sources & evidence

ORD record: ord-b6651b4036a144679903df2439faf0d7
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299086B2

Reaction notes

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