Hydrochloric Acid → HCID 69113097, compound

HRID 2377219Notes

Reaction equation

HRID 2377219 reaction equation
Cl.[C:2](O)(=O)C.[CH:6]1([CH2:12][C:13]2[CH:19]=[CH:18][C:16]([OH:17])=[CH:15][C:14]=2[OH:20])[CH2:11][CH2:10][CH2:9][CH2:8]C1>CO>[CH:12]1([C:13]2[CH:19]=[CH:18][C:16]([OH:17])=[C:15]([CH3:2])[C:14]=2[OH:20])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69113424HCID 69113424, compound

Product 1

HCID 69113097HCID 69113097, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3 M HCl (13 ml) was added to a solution of crude 4-cyclohexylmethyl resorcinol monoacetate (2.71 g) in methanol (70 ml) and the solution stirred at room temperature for 16 h. At this time, TLC showed the clean formation of product (Rf 0.14) and traces of starting material (Rf 0.48) (Note 11). The solvent was reduced to ⅓ volume under reduced pressure and partitioned between ethyl ether (300 ml) and 1 M HCl (100 ml), washed with saturated NaCl (100 ml), the aqueous layer back extracted with ethyl ether (200 ml), the organic layers dried (Na2SO4), filtered and the solvent removed to give 4-cyclohexyl methyl resorcinol as a light amber-colored oil which crystallized upon standing at room temperature (1.1 g, 75% yield). The crude product was purified by flash chromatography to give 4-cyclohexyl methyl resorcinol B2 as a white solid (617 mg, 51% yield) (Note 12): m.p. 112-113° C.; 1H NMR (60 MHz, acetone-d6) delta 1.08-1.76 (m, 11H), 2.44 (d, JJ=6.2 Hz, 2H), 6.26 (dd, JJ=7.9, 2.3 Hz, 1H), 6.39 (m, 1H), 6.86 (d, JJ=7.9 Hz, 1H), 7.90 (s, 1H); 13C NMR (60 MHz, acetone-d6) delta 27.3, 33.3, 38.2, 39.5, 102.9, 106.7, 119.0, 132.5, 157.0, 157.4; m/z (EI; TMS derivatized; M+) 350.

Workup

  1. custompartitioned between ethyl ether (300 ml) and 1 M HCl (100 ml)
  2. washwashed with saturated NaCl (100 ml)
  3. extractionthe aqueous layer back extracted with ethyl ether (200 ml)
  4. dry with materialthe organic layers dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removed

Sources & evidence

ORD record
ord-27b846368e62457388bd1bf92671e1b4
Source dataset
uspto-grants-2008_12
Patent number
US07468464B2

Reaction notes

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