tert-Butanol → HCID 68885070, compound

HRID 1757846Notes

Reaction equation

HRID 1757846 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:15]=[C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:17]=2)C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.C([N:45]([CH2:48]C)CC)C.[C:50]([OH:54])([CH3:53])([CH3:52])[CH3:51]>>[CH3:51][C:50]([O:54][C:48](=[O:33])[NH:45][C:11]1[CH:10]=[C:9]([O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:15]=1)([CH3:53])[CH3:52]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 993073,5-Bis(phenylmethoxy)benzoic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 68885070HCID 68885070, compoundYield 93%

Procedure

A mixture of 2.0 g (5.98 mmol) of 3,5-bis(phenylmethoxy)benzoic acid, 1.6 ml (7.18 mmol) of diphenylphosphoryl azide, 1.0 ml (7.18 mmol) of triethylamine and 6 ml (64 mmol) of t-butyl alcohol (freshly distilled from sodium)in 15 ml of anhydrous toluene was stirred at reflux under argon for 18 hours. The reaction mixture was washed with NaHCO3 solution, dried and concentrated at reduced pressure to an oil. Chromatography on 25 g of 230-400 mesh silica gel using 10% ethyl acetate-hexane gave 2.25 g (93% yield, mp 96°-98°) of 3,5-bis(phenylmethoxy) phenyl carbamicacid dimethylethyl ester.

Workup

  1. distillationfreshly distilled from sodium)in 15 ml of anhydrous toluene
  2. temperatureat reflux under argon for 18 hours
  3. washThe reaction mixture was washed with NaHCO3 solution
  4. customdried
  5. concentrationconcentrated at reduced pressure to an oil

Sources & evidence

ORD record
ord-678c1e6cbdf146e4a8ea242a5ee3f96c
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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