Hydrochloric Acid → Methyl 4-(5-Hydroxypent-1-en-2-yl)benzoate

HRID 2050534Notes

Reaction equation

HRID 2050534 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH2:11][CH2:12][CH2:13][C:14]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)=[CH2:15])(=O)C.Cl>CO>[OH:10][CH2:11][CH2:12][CH2:13][C:14]([C:16]1[CH:17]=[CH:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:24][CH:25]=1)=[CH2:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 15734962Methyl 4-(5-Acetoxy-pent-1-en-2-yl)benzoate

Product 1

HCID 15734963Methyl 4-(5-Hydroxypent-1-en-2-yl)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution containing 0.52 g (1.0 eq) of dry potassium carbonate in 100 ml of anhydrous methanol was added 1.0 g (1.0 eq) of methyl 4-(5-acetoxy-pent-1-en-2-yl)benzoate in anhydrous methanol. The resulting reaction mixture was stirred for two hours at room temperature, neutralized by the addition of 7.6 ml of 1N hydrochloric acid (2.0 eq), and extracted twice with dichloromethane. The extracts were dried over magnesium sulfate, and concentrated under reduced pressure to yield the product. mp. 28-30° C. M.S.:m/z= 220.1094, (M+ calc. for CH13H16O3 : 220.1099), 189 (M+ --CH3) ), 176 (100%), 145. 1H-N M.R.(CDCl3, 300 MHz): δ=1.56(s (broad), 1H, OH); 1.75(quin, 2H, CH2 --CH2 --CH2, J=7.5 Hz); 2.60(t, 2H, CH2 --C=, J=7.5 Hz); 3.68(t, broad), 2H, CH2OH, J=7.5 Hz; 3.94(s, 3H, CH3O); 5.20(s, 1Holef.); 5.42(s, 1Holef.); 7.48 (d, 2Harom., J=9 Hz); 8.00(d, 2Harom., J=9 Hz).

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted twice with dichloromethane
  3. dry with materialThe extracts were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto yield the product

Sources & evidence

ORD record
ord-3c2a10941fc2440d9a2179f92cbfece8
Source dataset
uspto-grants-1991_05
Patent number
US05013738

Reaction notes

Loading…