Benzyl Alcohol → HCID 21909277, compound

HRID 1982836Notes

Reaction equation

HRID 1982836 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=C(C=[CH:16][C:17]=1[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[CH:21][CH:20]=1)C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:29]([CH2:32][CH3:33])[CH2:30]C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:41])C=CC=CC=1.[CH2:51]([OH:58])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:32]([NH:29][C:30](=[O:41])[O:58][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH:33]=[CH:16][C:17]=1[CH2:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][CH3:26])=[CH:23][CH:24]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 17863616HCID 17863616, compound

Product 1

HCID 21909277HCID 21909277, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
100 °C

Procedure

To a solution of 3-benzyloxy-4-(4-ethylbenzyl)benzoic acid (1.4 g) and triethylamine (1.3 mL) in 1,4-dioxane (10 mL) was added diphenylphosphoryl azide (1.3 g) in 1,4-dioxane (10 mL), and the mixture was stirred at 100° C. for 1 hour. Benzyl alcohol (1.6 mL) was added to the reaction mixture, and the mixture was stirred at the same temperature for 7 hours. The solvent of the reaction mixture was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=4/1) to give benzyl N-[3-benzyloxy-4-(4-ethylbenzyl)phenyl]carbamate (1.4 g). To a solution of the obtained benzyl N-[3-benzyloxy-4-(4-ethylbenzyl)phenyl]carbamate (1.4 g) in methanol (15 mL) was added 10% palladium-carbon powder (0.28 g), and the mixture was stirred under a hydrogen atmosphere for 11 hours. Insoluble materials were removed by filtration, and the solvent of the filtrate was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1) to give 5-amino-2-(4-ethylbenzyl)-phenol (0.54 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 7 hours
  2. customThe solvent of the reaction mixture was removed under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-d6d667d3b6e247debab06b8bf9bcf20a
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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