Hydrochloric Acid → HCID 18614937, compound

HRID 1265252Notes

Reaction equation

HRID 1265252 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]2[C:20]3[C:15](=[CH:16][C:17]4[C:24]([CH3:26])([CH3:25])[CH2:23][CH2:22][C:21]([CH3:28])([CH3:27])[C:18]=4[CH:19]=3)[O:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=1.Cl>CO>[CH3:27][C:21]1([CH3:28])[C:18]2[CH:19]=[C:20]3[C:15](=[CH:16][C:17]=2[C:24]([CH3:26])([CH3:25])[CH2:23][CH2:22]1)[O:14][CH2:13][CH:12]=[C:11]3[CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:29])=[O:2])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53782765HCID 53782765, compound

Product 1

HCID 18614937HCID 18614937, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 4-(6,6,9,9-tetramethyl-6,7,8,9-tetrahydro-2H-benzo[g]chromen-4-ylidenemethyl)-benzoic acid methyl ester (220 mg, 0.56 mmol) in methanol (10 mL) was added concentrated HCl (0.05 mL) and the solution was allowed to stir at 85° C. for 12 h. The solution was quenched with aqueous saturated NaHCO3 solution (100 mL), extracted with EtOAc, dried (Na2SO4), and concentrated. The acid was obtained by hydrolysis according to the standard conditions and was purified by silica gel preparative TLC (50% EtOAc/Hexane) to afford 4-(6,7,8,9-tetrahydro-6,6,9,9-tetramethyl2H-benzo[g]chromen-4-ylmethyl)-benzoic acid (133) (89%) as a white solid: m.p. 200-201° C.; IR (neat) 2969 s, 2958 s, 2922 s, 2361 m, 1689 s, 1608 m, 1419 s, 1408 s, 1286 m, 1174 s, 1018 s cm−1; 1H NMR (400 MHz, CDCl3) δ 8.04 (½ ABq, 2H, J=8.0 Hz, ArH), 7.37 (½ ABq, 2H, J=8.0 Hz, ArH), 6.98 (s, 1H, ArH), 6,74 (s, 1H, ArH), 5.43 (broad t, 1H, olefinic), 4.75 (m, 2H, ring CH2), 3.79 (s, 2H, benzylic CH2), 1.59 (s, 4H, 2CH2), 1.22 (s, 6H, 2CH3), 1.13 (s, 6H, 2CH3).

Workup

  1. customThe solution was quenched with aqueous saturated NaHCO3 solution (100 mL)
  2. extractionextracted with EtOAc
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe acid was obtained by hydrolysis
  6. customwas purified by silica gel preparative TLC (50% EtOAc/Hexane)

Sources & evidence

ORD record
ord-1c015fa8e40f48d38c42430b1a9f18a6
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

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