Resorcinol → HCID 67367789, compound

HRID 410031Notes

Reaction equation

HRID 410031 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][C:13]([OH:15])=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[C:16]1([CH:23]=[CH:22][CH:21]=[C:19]([OH:20])[CH:18]=1)[OH:17].C([O-])([O-])=O.[Na+].[Na+]>B(F)(F)F.CCOCC>[OH:17][C:16]1[CH:18]=[C:19]([OH:20])[CH:21]=[CH:22][C:23]=1[C:13](=[O:15])[CH2:12][CH:9]1[CH2:8][CH2:7][CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 10340Sodium CarbonateHCID 158961924-CarboxyMethyl-cyclohexanecarboxylic acid ethyl ester

Product 1

HCID 67367789HCID 67367789, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 8000Boron trifluoride etherateSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 2-(4-(ethoxycarbonyl)cyclohexyl)acetic acid (700 mg, 11.6 mmol) in BF3-Et2O (10 ml) was added resorcinol (1.5 g, 14.0 mmol). The solution was stirred at 85° C. overnight, poured into Na2CO3 solution (2N, 20 ml), extracted with EtOAc (30 ml×3), washed with brine, dried over Na2SO4, filtrated and concentrated to afford 3 g of yellow oil, which was purified by silica gel column (PE/EtOAc=3/1) to afford 400 mg of Intermediate C. MS (ESI): m/z 307.1 [M+1]+.

Workup

  1. extractionextracted with EtOAc (30 ml×3)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltrated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d1ee714b17a747b38596c7ac669da982
Source dataset
uspto-grants-2014_06
Patent number
US08759548B2

Reaction notes

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