Phenol → HCID 20312393, compound

HRID 2420014Notes

Reaction equation

HRID 2420014 reaction equation
[CH2:1]([O:5][C:6](=[O:20])[CH:7](OC(=O)C)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:2][CH2:3][CH3:4].[C:21]1([OH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:1]([O:5][C:6](=[O:20])[CH:7]([C:24]1[CH:25]=[CH:26][C:21]([OH:27])=[CH:22][CH:23]=1)[NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:2][CH2:3][CH3:4].[CH2:1]([O:5][C:6](=[O:20])[CH:7]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[OH:27])[NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 996PhenolHCID 8000Boron trifluoride etherateHCID 20312395HCID 20312395, compound

Product 2

HCID 20312393HCID 20312393, compoundHCID 20312394N-t-butoxycarbonyl-2-(4-hydroxyphenyl)glycine n-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.5 g (0.005 mol.) of N-t-butoxycarbonyl-2-acetoxyglycine n-butyl ester in 10 ml. of methylene chloride was slowly added over a 1 hour period to a stirred solution of 0.6 g. (0.006 mol.) of phenol and 0.1 ml. of boron trifluoride etherate in 15 ml. of methylene chloride. After 3 hours the reaction mixture was chromatographed on 50 g. of silica gel and eluted with methylene chloride containing increasing amounts of ethyl acetate to give N-t-butoxycarbonyl-2-(4-hydroxyphenyl)-glycine n-butyl ester and N-t-butoxycarbonyl-2-(2-hydroxyphenyl)glycine n-butyl ester.

Workup

  1. customAfter 3 hours the reaction mixture was chromatographed on 50 g
  2. washof silica gel and eluted with methylene chloride containing
  3. temperatureincreasing amounts of ethyl acetate

Sources & evidence

ORD record
ord-a8ef7c4c0d5f4fb88241f352a71d8d43
Source dataset
uspto-grants-1978_08
Patent number
US04108854

Reaction notes

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