2-Butanone, 4-[2,5-bis(acetyloxy)-3,4,6-trimethylphenyl]- → 6-Hydroxy-2,5,7,8-tetramethylchroman-2-acetic acid

HRID 268424Notes

Reaction equation

C(O[C:5]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([O:13]C(=O)C)=[C:7]([CH3:17])[C:6]=1[CH2:18][CH2:19][C:20](=[O:22])[CH3:21])(=O)C.C[C:24](P(OC)(O)=O)([C:26]([O-:28])=[O:27])C>>[OH:13][C:8]1[C:7]([CH3:17])=[C:6]2[C:5](=[C:10]([CH3:11])[C:9]=1[CH3:12])[O:22][C:20]([CH3:21])([CH2:24][C:26]([OH:28])=[O:27])[CH2:19][CH2:18]2

Participants

Reactant 2

HCID 1044132-Butanone, 4-[2,5-bis(acetyloxy)-3,4,6-trimethylphenyl]-

HCID 53413272Trimethylphosphonoacetate

Product 1

HCID 55926-Hydroxy-2,5,7,8-tetramethylchroman-2-acetic acid

Procedure

By the procedure described in Example 6, (±)-4-(2,5-diacetoxy-3,4,6-trimethylphenyl)butan-2-one was treated with the anion from trimethylphosphonoacetate. The crude (±)-methyl 5-(2,5-diacetoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenoate thus obtained, upon saponification with base as in Example 6, yielded (±)-6-hydroxy-2,5,7,8-tetramethylchroman-2-acetic acid as a light tan powder, m.p. 169°-171.5°.

Workup

customThe crude (±)-methyl 5-(2,5-diacetoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenoate thus obtained, upon saponification with base as in Example 6

Sources & evidence

ORD record: ord-ccf75b6e8e3c499b948c276ca56aa6ac
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03947473

Reaction notes

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