Hydrochloric Acid → 2-(Dimethoxymethyl)-4,6-dihydroxy-2,5,7,8-tetramethylchroman

HRID 462583Notes

Reaction equation

HRID 462583 reaction equation
[CH3:1][O:2][CH:3]([O:20][CH3:21])[C:4]1([CH3:19])[CH2:13][C:12](=[O:14])[C:11]2[C:6](=[C:7]([CH3:18])[C:8]([CH3:17])=[C:9]([OH:16])[C:10]=2[CH3:15])[O:5]1.[BH4-].[Na+].[OH-].[Na+].Cl>CO>[CH3:21][O:20][CH:3]([O:2][CH3:1])[C:4]1([CH3:19])[CH2:13][CH:12]([OH:14])[C:11]2[C:6](=[C:7]([CH3:18])[C:8]([CH3:17])=[C:9]([OH:16])[C:10]=2[CH3:15])[O:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydride2×HCID 130515362-(Dimethoxymethyl)-6-hydroxy-2,5,7,8-tetramethyl-chroman-4-one

Product 1

HCID 130515402-(Dimethoxymethyl)-4,6-dihydroxy-2,5,7,8-tetramethylchromanYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

9.4 g (32 mmoles) of the product from Example 2 were reacted with 2.43 g (64 mmoles) NaBH4 in 100 ml of methanol at 20°-60° C. After 6 hours, a further 2.43 g of NaBH4 were added, after which the reaction mixture was stirred at room temperature for 16 hours. 100 ml of 3N NaOH were then added, and the mixture was neutralized with dilute hydrochloric acid and then extracted with ether, a brown oil being obtained as the crude product in 95% yield. IR: 3,600 (broad) cm-1.

Workup

  1. extractionextracted with ether

Sources & evidence

ORD record
ord-3b31a94508974d0fa5a521efc2916cd5
Source dataset
uspto-grants-1985_05
Patent number
US04515975

Reaction notes

Loading…