Acetic Anhydride → HCID 14692990, compound

HRID 1608071Notes

Reaction equation

HRID 1608071 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH3:8][C:9]1([CH3:23])[CH:14]=[C:13]([CH3:15])[CH2:12][C:11]([CH3:17])([CH3:16])[CH:10]1[C:18](=C)[CH2:19]CO.C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[C:5]([O:4][CH2:1][CH2:2][C:18](=[CH2:19])[CH:10]1[C:11]([CH3:17])([CH3:16])[CH2:12][C:13]([CH3:15])=[CH:14][C:9]1([CH3:23])[CH3:8])(=[O:7])[CH3:6]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 14692978HCID 14692978, compound

Product 1

HCID 14692990HCID 14692990, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of acetic anhydride (0.23 mL) in dichloromethane (2 mL) was reacted with a mixture of 2,2,4,6,6-pentamethyl-γ-methylene-3-cyclohexene-1-propanol (0.56 g, 0.0025 mol), triethylamine (0.41 mL), 4-dimethylaminopyridine (0.031 g) and dichloromethane at 25° C. Work-up, chromatography and distillation gave 0.60 g of 2,2,4,6,6-pentamethyl-γ-methylene-3-cyclohexene-1-propanol acetate bp (kugelrohr bath 110°-120° C.), 0.5 mm (GLC purity: 88%). 1H-NMR (60 MHz, CDCl3) δ0.93 (6H, s), 1.00 and 1.02 (6H, 2s), 1.60 (3H, s), 2.00 (3H, s), 0.9-2.6 (5H, m), 4.20 (1H, t, J=7 Hz), 4.86-5.07 (3H, m); IR (film) vmax 2960, 1735, 1635, 1440, 1370, 1350 cm-1 ; MS (m/e) 264, 249, 221, 204, 189, 108, 96.

Workup

  1. distillationchromatography and distillation

Sources & evidence

ORD record
ord-c4d05ccbf45844948c91e7801c237838
Source dataset
uspto-grants-1989_09
Patent number
US04868339

Reaction notes

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