Methanol → HCID 85701783, compound

HRID 714029Notes

Reaction equation

HRID 714029 reaction equation
[OH:1][C:2]1[C:3]([CH2:11][CH2:12][CH3:13])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:18]O>>[OH:1][C:2]1[C:3]([CH2:11][CH2:12][CH3:13])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:18])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 15867527HCID 15867527, compound

Product 1

HCID 85701783HCID 85701783, compoundYield 87%

Procedure

Cool a solution of 3-hydroxy-2-propyl-benzoic acid (59.79 g, 332 mmol) in MeOH (598 mL) to −10° C. and add thionyl chloride (36.26 mL, 497.1 mmol) using a syringe pump over 35 min. Allow the mixture to warm to ambient temperature while stirring over 35 h. Concentrate the mixture in vacuo and dilute the residue with methyl-tert-butylether (360 mL). Concentrate the resultant mixture in vacuo to dryness to yield the title compound (64.4 g, 87%) as a tan solid. 1H NMR (300 MHz, CDCl3) δ 7.38 (dd, J=8.0, 0.8 Hz, 1H); 7.10 (t, J=8.0 Hz, 1H); 6.93 (dd, J=8.0, 0.8 Hz, 1H); 5.1 (bs, 1 H); 3.89 (s, 3H); 2.98 (m, 2H), 1.61 (m, 2H); 1.00 (t, J=7.4 Hz, 3H).

Workup

  1. customover 35 min
  2. concentrationConcentrate the mixture in vacuo
  3. additiondilute the residue with methyl-tert-butylether (360 mL)
  4. concentrationConcentrate the resultant mixture in vacuo to dryness

Sources & evidence

ORD record
ord-33071ad68ee444678a2de123dc0c3196
Source dataset
uspto-grants-2015_11
Patent number
US09187411B2

Reaction notes

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