Water → tert-Butyl 4-(prop-1-en-2-yl)phenyl carbonate

HRID 2412346Notes

Reaction equation

HRID 2412346 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([CH3:8])=[CH2:7])=[CH:4][CH:3]=1.[OH:11][C:12]1C=CC(C(C2C=CC(O)=CC=2)(C)C)=CC=1.[CH3:28][C:29]([CH3:32])([O-:31])[CH3:30].[K+].O>O1CCCC1.C(OCC)(=O)C>[C:29]([O:31][C:12]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([CH3:8])=[CH2:7])=[CH:4][CH:3]=1)=[O:11])([CH3:32])([CH3:30])[CH3:28]

Participants

7

Reactant 4

HCID 962WaterHCID 6623Bisphenol AHCID 584247p-IsopropenylphenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 14419264tert-Butyl 4-(prop-1-en-2-yl)phenyl carbonateYield 81%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5.64 g of p-hydroxy-α-methylstyrene, synthesized by base-catalyzed cleavage of 2,2-bis(p-hydroxyphenyl)propane, and 6.5 g of potassium tert-butoxide in 50 mL of dry tetrahydrofuran was stirred for 10 minutes, then a tetrahydrofuran solution of 12.7 g of di-tert-butyl dicarbonare was added. The resulting gelatinous mixture was mechanically stirred for 20 minutes, and then poured into cold water. After work-up, a crude product was obtained by evaporation of the extraction solvent (ethyl acetate). Purification was achieved by high pressure liquid chromatography with hexane as eluent to give 8.03 g (81%) of the pure p-tert-butoxycarbonyloxy-α-methylstyrene.

Workup

  1. stirringThe resulting gelatinous mixture was mechanically stirred for 20 minutes
  2. customPurification

Sources & evidence

ORD record
ord-13037c2afd2741ecb764fb9b41e30eb9
Source dataset
uspto-grants-1985_01
Patent number
US04491628

Reaction notes

Loading…