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

HRID 2037343Notes

Reaction equation

[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH3:12])[C:10]=1[OH:11])[CH:6]=[O:7])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C.O.CC(=O)OCC>[CH2:19]([O:11][C:10]1[C:9]([CH3:12])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH2:1][CH3:2])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-ethyl-4-hydroxy-5-methyl-benzaldehyde (25.0 g, 152 mmol) in acetonitrile (250 mL), K2CO3 (42.1 g, 305 mmol) followed by benzyl bromide (26.0 g, 152 mmol) is added. The suspension is stirred at 60° C. for 18 h. The mixture is diluted with water (150 mL) and EA (150 mL). The org. extract is separated and the aq. phase is extracted once more with EA (100 mL). The combined org. extracts are washed with water (150 mL) and concentrated. 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 (27.2 g) as a yellow oil; LC-MS: tR=1.09 min; 1H NMR (D6-DMSO): δ1.19 (t, J=7.5 Hz, 3H), 2.35 (s, 3H), 2.70 (q, J=7.5 Hz, 2H), 4.90 (s, 2H), 7.37-7.41 (m, 1H), 7.42-7.46 (m, 2H), 7.49-7.52 (m, 2H), 7.65-7.69 (m, 2H), 9.92 (s, 1H).

Workup

additionis added
extractionextract
customis separated
extractionthe aq. phase is extracted once more with EA (100 mL)
washextracts are washed with water (150 mL)
concentrationconcentrated
customThe crude product is purified by CC on silica gel eluting with heptane:EA 9:1

Sources & evidence

ORD record: ord-34ae26f8d4f44d47a3bf4cbd46e2f25b
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575200B2

Reaction notes

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