3-Hydroxybenzaldehyde → 3-(1-Methyl-cyclohexylmethoxy)-benzaldehyde

HRID 1009184Notes

Reaction equation

[CH3:1][C:2]1([CH2:8][O:9]S(C(F)(F)F)(=O)=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.O[C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=[O:22].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:1][C:2]1([CH2:8][O:9][C:18]2[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=2)[CH:21]=[O:22])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of compound iii (0.5 mmol), 3-hydroxy-benzaldehyde (iv, 0.6 mmol) and K2CO3 (0.7 mmol) were dissolved in DMF (3 mL). The solution was heated to 80° C. for 4 hr. The solution was poured into water, extracted with ethyl acetate (10 mL) three times, and concentrated. The residue was purified by chromatography and resulted in 0.22 mmol of 3-(1-methyl-cyclohexylmethoxy)-benzaldehyde (v) with a 44% yield.

Workup

extractionextracted with ethyl acetate (10 mL) three times
concentrationconcentrated
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-edbca64020464f188b204f229474d3e7
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973062B2

Reaction notes

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