Methanol → HCID 58550770, compound

HRID 72928Notes

Reaction equation

HRID 72928 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

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 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 reaction mixture was heated in a microwave vial at 100° C. for 15.5 hours. The reaction mixture was concentrated in vacuo and the crude product was purified by silica gel column chromatography using 0-30% ethyl acetate in hexane as eluent 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

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8f437b7a9df4446c9bc6696cce8d6602
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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