Acetic Anhydride → (+/-)-Methyl-(6-acetoxy-2, 5,7,8-tetramethylchroman-2-yl) acetate

HRID 328842Notes

Reaction equation

HRID 328842 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:19])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([OH:18])([CH3:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2].C[O:21][C:22]([CH2:24]P(OC)(OC)=O)=O.[C:31](OC(=O)C)(=O)C>N1C=CC=CC=1>[C:22]([O:18][C:10]1([CH3:17])[CH:9]([CH3:31])[CH2:8][C:7]2[C:12](=[C:13]([CH3:16])[C:14]([CH3:15])=[C:5]([O:4][C:1](=[O:3])[CH3:2])[C:6]=2[CH3:19])[O:11]1)(=[O:21])[CH3:24]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 80029Trimethyl phosphonoacetateHCID 144156666-Acetoxy-2-hydroxy-2,5,7,8-tetramethylchroman

Product 1

HCID 54353318(+/-)-Methyl-(6-acetoxy-2, 5,7,8-tetramethylchroman-2-yl) acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

By the procedure of Example 6, 26.43 g. (0.10 mol.) of (±)-6-acetoxy-2-hydroxy-2,5,7,8-tetramethylchroman was reacted with trimethyl phosphonoacetate and then with 80 ml. of pyridine and 120 ml. of acetic anhydride by stirring under N 2 overnight. The solution was poured into ice-H 2 O and worked up and dried in the manner of Example 2. The crude product was filtered throgh 750 g. of 0.05-0.2 mm silica gel with 95:5 parts by volume benzene ether and then distilled to give (±)-methyl-(6-acetoxy-2, 5,7,8-tetramethylchroman-2-yl) acetate as a colorless resin: b.p. 147°-149°C./10 mmHg.

Workup

  1. customdried in the manner of Example 2
  2. filtrationThe crude product was filtered throgh 750 g
  3. distillationof 0.05-0.2 mm silica gel with 95:5 parts by volume benzene ether and then distilled

Sources & evidence

ORD record
ord-4b662c9a777d4099abdde8edd4867afa
Source dataset
uspto-grants-1977_04
Patent number
US04018799

Reaction notes

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