Methanol → HCID 58550770, compound

HRID 2204174Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]([CH3:17])=[CH2:16])[C:6]([O:8][CH3:9])=[O:7].OS(O)(=O)=O.[CH3:23][OH:24]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]([O:24][CH3:23])([CH3:17])[CH3:16])[C:6]([O:8][CH3:9])=[O:7]

Participants

Reactant 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 51109732Methyl 3-methoxy-4-(2-methylallyloxy)benzoate

Product 1

HCID 58550770HCID 58550770, compoundYield 59%

Conditions

Temperature: 100 °C

Procedure

To methyl 3-methoxy-4-(2-methylallyloxy)benzoate (313 mg, 1.33 mmol) in MeOH (2.5 mL) was added H2SO4 (71 μL, 1.3 mmol) and the mixture was heated in a microwave vial at 100° C. for 15.5 h. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography on silica gel (0-30% ethyl acetate in hexane) to yield methyl 3-methoxy-4-(2-methoxy-2-methyl-propoxy)benzoate (208 mg, 59%). ESI-MS m/z calc. 268.1, found 269.5 (M+1)+; Retention time: 1.46 minutes (3 min run). 1H NMR (400 MHz, DMSO) δ 7.57 (dd, J=8.4, 2.0 Hz, 1H), 7.45 (d, J=1.9 Hz, 1H), 7.10 (d, J=8.5 Hz, 1H), 3.90 (s, 2H), 3.83 (s, 3H), 3.82 (s, 3H), 3.17 (s, 3H), 1.22 (s, 6H).

Workup

customThe solvent was evaporated under reduced pressure
customthe crude product was purified by column chromatography on silica gel (0-30% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-be22004ad3134dc78b7ea59a9ad5f020
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365588B2

Reaction notes

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