Water → HCID 14296103, compound

HRID 1160614Notes

Reaction equation

HRID 1160614 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C=O)C>[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:9])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1511384-Hydroxycyclohexanecarboxylic acid

Product 1

HCID 14296103HCID 14296103, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxycyclohexane carboxylic acid (19.95 g, 138.4 mmol) in 100 mL of degassed DMF was added potassium carbonate (21.0 g, 152.2 mmol) and benzyl bromide (15.61 mL, 131.4 mmol). After 16 hours at room temperature, the reaction mixture was poured into 500 mL of water and extracted 3 times with EtOAc. The combined organic layers were washed with water and brine prior to drying over sodium sulfate. Filtration and solvent removal provided benzyl 4-hydroxycyclohexane carboxylate as a clear oil.

Workup

  1. extractionextracted 3 times with EtOAc
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialto drying over sodium sulfate
  4. filtrationFiltration and solvent removal

Sources & evidence

ORD record
ord-01a4462491914b17b2aa8ddf13e7c84b
Source dataset
uspto-grants-2010_10
Patent number
US07816380B2

Reaction notes

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