Methanol → HCID 178501285, compound

HRID 2404149Notes

Reaction equation

HRID 2404149 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.O=S(Cl)Cl.[CH3:15]O>>[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH3:15])=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178525780HCID 178525780, compound

Product 1

HCID 178501285HCID 178501285, compoundYield 100%

Conditions

Temperature
70 °C

Procedure

To a solution of (trans)-4-hydroxycyclohexanecarboxylic acid (4.32 g, 30 mmol) in MeOH (20 mL) was added SOCl2 (7.08 g, 60 mmol, 2.0 eq) dropwise at rt. Then the mixture was stirred at 70° C. for 18 h, and the solvent was removed in vacuo to give the title compound as a colorless oil (4.74 g, yield: 100%). 1H NMR (400 MHz, DMSO-d6) δ: 4.33 (br, 1H), 3.68-3.60 (m, 1H), 3.57 (s, 3H), 2.37-2.31 (m, 1H), 1.82-1.74 (m, 2H), 1.53-1.45 (m, 6H).

Workup

  1. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-59a3fa0cda8d4088a3ee1a128c2d9d82
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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