Diazomethane → Methyl 2,6-dihydroxy-4-pentylbenzoate

HRID 488671Notes

Reaction equation

HRID 488671 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:8]=[C:7]([OH:16])[C:3]=1[C:4]([OH:6])=[O:5].[N+](=[CH2:19])=[N-]>CCOCC>[OH:1][C:2]1[CH:10]=[C:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:8]=[C:7]([OH:16])[C:3]=1[C:4]([O:6][CH3:19])=[O:5]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 3046173Benzoic acid, 2,6-dihydroxy-4-pentyl-

Product 1

HCID 22271912Methyl 2,6-dihydroxy-4-pentylbenzoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2,6-dihydroxy-4-pentylbenzoic acid (2.0 g, 8.9 mM) in ether was treated with a 0.3 M solution of diazomethane in ether (30 mL) and stirred for 10 minutes. Nitrogen was bubbled through the solution for 10 minutes and then glacial acetic acid (4 drops). The reaction was concentrated under reduced pressure and purified by chromatography (5% ethyl acetate in hexanes) to give the desired product. MS ESI(−)) m/e 237 (M−H)+; 1H NMR (300 MHz, CDCl3) δ 9.62 (bs, 2H), 6.33 (s, 2H), 4.06 (s, 3H), 2.50 (t, 2H), 1.64-1.55 (m, 2H), 1.34-1.27 (m, 4H), 0.92-0.87 (m, 3H).

Workup

  1. customNitrogen was bubbled through the solution for 10 minutes
  2. concentrationThe reaction was concentrated under reduced pressure
  3. custompurified by chromatography (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5fb5e418febd41c7b9ce1a8113a7047f
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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