Ethanol → HCID 178472486, compound

HRID 2095646Notes

Reaction equation

HRID 2095646 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.[CH3:11][CH2:12]O.S(=O)(=O)(O)O.C([O-])([O-])=O.[Na+].[Na+]>>[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 178525779HCID 178525779, compound

Product 1

HCID 178472486HCID 178472486, compound

Conditions

Temperature
70 °C

Procedure

To a solution of cis-4-hydroxycyclohexanecarboxylic acid (4.00 g, 27.7 mmol) in EtOH (20 mL, 300 mmol) was added sulfuric acid (0.1 mL, 2 mmol), and the solution was heated to 70° C. for 2 h. After cooling to rt, Na2CO3 solution was added slowly to bring to pH=8. The organic solvent was removed in vacuo, and the material was extracted with EtOAc and washed with water. The organic layer was concentrated in vacuo to afford the title compound as a clear oil. 1H NMR (400 MHz, DMSO-d6): δ=1.17 (t, J=7.1 Hz, 3H), 1.42-1.56 (m, 6H), 1.73-1.86 (m, 2H), 2.26-2.39 (m, 1H), 3.60-3.71 (m, 1H), 4.04 (q, J=7.1 Hz, 2H), 4.38 (d, J=3.5 Hz, 1H).

Workup

  1. temperatureAfter cooling to rt
  2. customThe organic solvent was removed in vacuo
  3. extractionthe material was extracted with EtOAc
  4. washwashed with water
  5. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-04677719d47247b38005f82f21479c6a
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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