Methanol → Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

HRID 574981Notes

Reaction equation

HRID 574981 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.S(Cl)(Cl)=O.[CH3:16]O>>[OH:1][CH2:2][CH:3]1[CH2:4][CH2:5][CH:6]([C:9]([O:11][CH3:16])=[O:10])[CH2:7][CH2:8]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 202819Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-

Product 1

HCID 11073869Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.). solution of 4-(hydroxymethyl)cyclohexanecarboxylic acid (40 g) in methanol (632 mL) was added thionyl chloride (22.15 mL) dropwise via an addition funnel. The reaction was slowly warmed to room temperature, stirred for 1 hour, concentrated by rotary evaporation, and the residue was purified by regular phase flash column chromatography (Analogix, 0-100% hexanes/ethyl acetate).

Workup

  1. temperatureThe reaction was slowly warmed to room temperature
  2. concentrationconcentrated by rotary evaporation
  3. customthe residue was purified by regular phase flash column chromatography (Analogix, 0-100% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-54f5c99b5fa04171a82bfd93b27c55da
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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