Methanol → HCID 22145715, compound

HRID 1994331Notes

Reaction equation

HRID 1994331 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([OH:11])[C:8]([O:12][CH:13]([CH3:15])[CH3:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:21]O>>[CH3:21][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([O:12][CH:13]([CH3:15])[CH3:14])[C:9]([OH:11])=[CH:10][C:2]=1[F:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 22145906HCID 22145906, compound

Product 1

HCID 22145715HCID 22145715, compound

Procedure

2-Fluoro-4-hydroxy-5-isopropyloxybenzoic acid (5.7 g) is dissolved in methanol (200 mL) and concentrated sulfuric acid (1 mL) and heated at 70° C. for 5 hours. The solution is concentrated and the resultant oil subjected to mplc on silica gel using petroleum ether: ethyl acetate (4:1 v/v) as eluent to give methyl-2-fluoro-4-hydroxy-5-isopropyloxybenzoate (5.7 g). [NMR (CDCl3) 7.38 (d, 1H, J=7 Hz), 6.67 (d, 1H, J=12 Hz), 4.85 (m, 1H), 3.9 (s, 3H), 1.3 (d, 6H, J=7 Hz)].

Workup

  1. concentrationThe solution is concentrated

Sources & evidence

ORD record
ord-d8f328a031ac4e0fa23e6008d80607bc
Source dataset
uspto-grants-2010_01
Patent number
US07652144B2

Reaction notes

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