Acetic Anhydride → HCID 19787828, compound

HRID 1656314Notes

Reaction equation

HRID 1656314 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][CH2:18][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[C:26](OC(=O)C)(=[O:28])[CH3:27]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.[OH-].[Na+]>[C:26]([O:11][C:10]1[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:6][C:7]([CH2:16][CH2:17][CH2:18][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[CH:8][C:9]=1[C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:28])[CH3:27]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 19787829HCID 19787829, compound

Product 1

HCID 19787828HCID 19787828, compoundYield 93.4%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A vigourously stirred mixture of 40.74 g (0.117 mol) of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-(tetrahydropyran-2-yloxy)propane and 5.85 g (16.7 mmol) of tetrabutylammonium hydrogen sulphate in 250 ml of dichloromethane and 250 ml of 50% aqueous sodium hydroxide is treated at 0° C. dropwise with 14.32 g (0.140 mol) of acetic anhydride, dissolved in 100 ml of dichloromethane, under a nitrogen atmosphere. After addition is complete, the mixture is reacted for an additional 4--hour period at ambient temperature. Following usual extradtive work-up, 42.69 g (93%) of 3-(4-acetoxy-3,5-di-tert-butylphenyl)-l-(tetrahydropyran-2-yloxy)propane is obtained as a brown viscous liquid, which is used for the following deprotection step without further purification. (C24H38O4 ; F.W. 390.6).

Workup

  1. additionAfter addition
  2. customthe mixture is reacted for an additional 4
  3. customat ambient temperature

Sources & evidence

ORD record
ord-557d53676f4f4972a4973be90245b753
Source dataset
uspto-grants-1993_10
Patent number
US05254549

Reaction notes

Loading…