Methylparaben → HCID 18177796, compound

HRID 394952Notes

Reaction equation

HRID 394952 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:15][OH:16])[CH:8]=2)[O:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:43]1[CH:52]=[CH:51][C:46]([C:47]([O:49][CH3:50])=[O:48])=[CH:45][CH:44]=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.CCOCC>[CH3:1][C:2]1([CH3:22])[CH2:11][C:10]([CH3:12])([CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:15][O:16][C:43]3[CH:52]=[CH:51][C:46]([C:47]([O:49][CH3:50])=[O:48])=[CH:45][CH:44]=3)[CH:8]=2)[O:3]1

Participants

7

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18177940HCID 18177940, compound

Product 1

HCID 18177796HCID 18177796, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.5 g of (RS)-2-(2,2,4,4-tetramethyl-chroman-6-yl)-heptanol dissolved in 35 ml THF were treated with 480 mg of triphenylphosphine, 275 mg of methyl 4-hydroxybenzoate and 0.28 ml of diethyl azodicarboxylate. The reaction mixture was heated to reflux for 6 hours. The mixture was diluted with 100 ml of ether and washed with two portions of 30 ml of water and one portion of 30 ml of sat. aq. sodium chloride solution. The organic phase was dried over MgSO4. The solvents were removed in vacuo and the resulting yellow oil was purified by flash chromatography (SiO2, 10% ethyl acetate/hexanes), giving 550 mg of (RS)-methyl 4-[2-(2,2,4,4-tetramethyl-chroman-6-yl)-heptyloxy]-benzoate as a pale yellow oil. 1H NMR (CDCl3): 7.95 (d, J=8.8 Hz, 2H), 7.10 (d, J=2.2 Hz, 1H), 6.94 (dd, J=8.3, 2.2 Hz, 1H), 6.88 (d, J=8.8 Hz, 2H), 6.73 (d, J=8.3 Hz, 1H), 4.20-4.00 (m, 2H), 3.87 (s, 3H), 3.05-2.90 (m, 1H), 1.95-1.85 (m, 1H), 1.82 (s, 2H), 1.70-1.60 (m, 1H), 1.34 (s, 6H), 1.33 (s, 3H), 1.32 (s, 3H), 1.30-1.20 (m, 6H), 0.90-0.80 (m, 3H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 hours
  3. washwashed with two portions of 30 ml of water and one portion of 30 ml of sat. aq. sodium chloride solution
  4. dry with materialThe organic phase was dried over MgSO4
  5. customThe solvents were removed in vacuo
  6. customthe resulting yellow oil was purified by flash chromatography (SiO2, 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0f3c3563561a48ae99580be3baea0dab
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

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