Acetic Anhydride → HCID 10136159, compound

HRID 2380722Notes

Reaction equation

[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][C:9]1[CH:10]=[C:11]([CH:17]2[C:21]3[CH:22]=[C:23]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:24]=[C:25]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]=3[O:19][C:18]2=[O:34])[CH:12]=[C:13]([CH3:16])[C:14]=1[OH:15]>C1(C)C(C)=CC=CC=1.CS(O)(=O)=O>[C:1]([O:15][C:14]1[C:13]([CH3:16])=[CH:12][C:11]([CH:17]2[C:21]3[CH:22]=[C:23]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:24]=[C:25]([C:26]([CH3:27])([CH3:28])[CH3:29])[C:20]=3[O:19][C:18]2=[O:34])=[CH:10][C:9]=1[CH3:8])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 105 °C

Procedure

53.6 g (0.53 mol) of acetic anhydride are added dropwise over a period of about 10 minutes to a suspension of 183.3 g (0.50 mol) of 3-(3,5-dimethyl-4-hydroxyphenyl)-5,7-di-tert-butylbenzofuran-2-one (compound (107), Table 1, Example 2) in 250 ml of xylene and 0.5 ml (7.7 mmol) of methanesulfonic acid which is stirred at 105° C. under a nitrogen atmosphere. The clear, colourless reaction mixture is concentrated at about 170° C. under a slight vacuum. 500 ml of 1-butanol are carefully added to the residue and the mixture is cooled with ice/water. The precipitated product is filtered and washed with 100 ml of 1-butanol. Drying gives 197.6 g (97%) of 3-(4-acetoxy-3,5-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one, melting point 165°-166° C. (compound (109), Table 1).

Workup

concentrationThe clear, colourless reaction mixture is concentrated at about 170° C. under a slight vacuum
addition500 ml of 1-butanol are carefully added to the residue
temperaturethe mixture is cooled with ice/water
filtrationThe precipitated product is filtered
washwashed with 100 ml of 1-butanol
customDrying

Sources & evidence

ORD record: ord-ff688b1cc3ad401dba0e20b8a8f25ae6
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05369159

Reaction notes

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