Ethanol → Ethyl 4-hydroxycyclohexanecarboxylate

HRID 1015367Notes

Reaction equation

HRID 1015367 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.S(=O)(=O)(O)O.C([O-])([O-])=O.[Na+].[Na+].[CH2:22](O)[CH3:23]>>[CH2:22]([O:9][C:8]([CH:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1)=[O:10])[CH3:23]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 1511384-Hydroxycyclohexanecarboxylic acid

Product 1

HCID 86973Ethyl 4-hydroxycyclohexanecarboxylateYield 100%

Procedure

4-Hydroxycyclohexane carboxylic acid (5 g, 34.5 mmol) was heated to reflux for 16 hours in the presence of 50 mL of ethyl alcohol and 2 mL of sulfuric acid. Reaction volume was reduce by half at reduced pressure and mixture was poured into sat. Na2CO3. Mixture was extracted 3×50 mL of ethyl acetate and combined organics were washed with brine and dried over MgSO4. Title compound was obtained as a colorless crude oil. (5.9 g; 100% yield).

Workup

  1. customReaction volume
  2. extractionMixture was extracted 3×50 mL of ethyl acetate
  3. washcombined organics were washed with brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-206bfade334042e5a9db4815577acadb
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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